3-(3-chlorophenyl)propan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL, 6.0 mmol) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An addition 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1 M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20–7.22 (m, 3H),7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h was added the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL, 6.0 mmol) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An addition 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1 M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20–7.22 (m, 3H),7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h was added the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL, 6.0 mmol) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An addition 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H),7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h was added the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromomethyl-benzoic acid methyl ester (0.115 g, 0.5 mmol), 3-(3-chloro-phenyl)-propylamine (0.102 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (3 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-[3-(3-chloro-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.105 g, 71%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.96 (m, 2H), 2.69 (t, 2H), 3.66 (t, 2H), 4.36 (s, 2H), 7.12-7.58 (m, 7H), 7.84 (d, 1H). GC-MS: m/z 285 (M)+. was heated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide prepared of Preparation 12, Step A (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An additional 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H), 7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide prepared of Preparation 12, Step A (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An additional 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H), 7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide prepared of Preparation 12, Step A (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An additional 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H), 7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0M solution of LiAlH4 in THF (6.0 mL, 6.0 mmol) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An addition 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H),7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h was added the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide prepared of Preparation 12, Step A (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An additional 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ 7.20-7.22 (m, 3H), 7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H); MS 170 (M+1). the reaction was stirred for 18 h the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of LiAlH4 in THF (6.0 mL, 6.0 mmol) was added dropwise to a suspension of 3-(3-chloro-phenyl)-acrylamide (1.0 g, 5.51 mmol) in 30 mL THF at 0° C. The reaction was warmed to room temperature and was stirred for 5 h. An additional 4 mL of 1 M LiAlH4 was added and the reaction was stirred for 18 h. An addition 2 mL of 1 M LiAlH4 was added and the reaction was stirred for 24 h. The reaction mixture was quenched by dropwise addition of water. The mixture was concentrated in vacuo to remove THF and was diluted with water. The aqueous solution was extracted with EtOAc. The organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in CHCl3 and the organic solution was washed with 1M HCl. The aqueous solution was basified to pH 11 with 1M NaOH and the product was extracted into CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a yellow oil (0.134 g). 1H NMR (400 MHz, CDCl3) δ7.20-7.22 (m, 3H),7.16 (m, 1H), 2.74 (t, 2H), 2.61 (t, 2H), 1.74 (m, 2H), MS 170 (M+1). the reaction was stirred for 18 h was added the reaction was stirred for 24 h The reaction mixture was quenched by dropwise addition of water The mixture was concentrated in vacuo to remove THF was diluted with water The aqueous solution was extracted with EtOAc The organic solution was washed with water dried over MgSO4 filtered concentrated in vacuo The residue was dissolved in CHCl3 the organic solution was washed with 1M HCl the product was extracted into CHCl3 The organic solution was dried over MgSO4 filtered concentrated in vacuo