3-phenylbutan-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 mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc. HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration

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

Procedure: A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.178 g, 0.5 mmol), 3-phenyl-butylamine (0.090 g, 0.6 mmol), and K2CO3 (0.166 g, 1.2 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-2-(3-phenyl-butyl)-2,3-dihydro-isoindol-1-one (0.046 g, 23%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.32 (d, 3H), 1.96 (m, 2H), 2.78 (m, 1H), 3.54 (m, 2H) 4.16 (s, 2H), 7.14-7.38 (m, 7H), 7.88 (d, 1H). GC-MS: m/z 391 (M)+. was heated

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

Procedure: A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.178 g, 0.5 mmol), 3-phenyl-butylamine (0.090 g, 0.6 mmol), and K2CO3 (0.166 g, 1.2 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-2-(3-phenyl-butyl)-2,3-dihydro-isoindol-1-one (0.046 g, 23%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.32 (d, 3H), 1.96 (m, 2H), 2.78 (m, 1H), 3.54 (m, 2H) 4.16 (s, 2H), 7.14-7.38 (m, 7H), 7.88 (d, 1H). GC-MS: m/z 391 (M)+. was heated

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

Procedure: A mixture of 3-phenylbutyraldehyde (3 ml, 20.18 mmol), ammonium acetate (15 g, 195 mmol) and sodium cyanoborohydride (900 mg, 14.32 mmol) in methanol (50 ml) was stirred overnight under an argon atmosphere. The reaction was acidified to pH 2 by the addition of conc HCl. The solvent was evaporated, dichloromethane and water were added, and the aqueous layer was made basic (pH 12) by the addition of solid potassium hydroxide. Extraction (dichloromethane) and concentration gave the title compound as an oil. ES-MS (m/z): 150.2 (M+H)+; 1H NMR (CDCl3): d 7.40-7.17 (m, 5H, Ph), 2.81 (q, 1H, CH), 2.62 (m, 2H, CH2), 1.76 (dq, 2H, CH2), 1.29 (d, 3H, CH3). The solvent was evaporated dichloromethane and water were added by the addition of solid potassium hydroxide Extraction (dichloromethane) and concentration