3-(3-methoxyphenyl)propan-1-amine

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-methoxy-phenyl)-propylamine (0.110 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-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.088 g, 62%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.0 (m, 2H), 2.66 (t, 2H), 3.64 (t, 2H), 3.82 (s, 3H), 4.36 (s, 2H), 6.78 (m, 2H), 7.16-7.58 (m, 5H), 7.84 (d, 1H). GC-MS: m/z 281 (M)+. was heated

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-methoxy-phenyl)-propylamine (0.110 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-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.088 g, 62%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.0 (m, 2H), 2.66 (t, 2H), 3.64 (t, 2H), 3.82 (s, 3H), 4.36 (s, 2H), 6.78 (m, 2H), 7.16-7.58 (m, 5H), 7.84 (d, 1H). GC-MS: m/z 281 (M)+. was heated

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

Procedure: A mixture of trans-3-(3-Methoxyphenyl)-2-propenenitrile (27.6 g, 173 mmol) and PtO2 (2.76 g) in 200 mL of EtOH and 30 mL of CHCl3 was shaken in a Parr apparatus under an atmosphere of 50-60 psi H2 overnight at RT. The reaction mixture was filtered through Celite and concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic layers were then dried over MgSO4, filtered and concentrated in vacuo to provide 24.2 g of the desired product as a yellow oil (85% yield). 1H NMR (CDCl3) δ 7.15-7.22 (m, 1H), 6.70-6.80 (m, 3H), 3.80 (s, 3H), 2.72 (t, J=6.0 Hz, 2H), 2.58-2.65 (m, 2H), 1.70-1.85 (m, 2H). The reaction mixture was filtered through Celite concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH The organic phase was separated the aqueous phase was extracted with CH2Cl2 (3×100 mL) The combined organic layers were then dried over MgSO4 filtered concentrated in vacuo

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

Procedure: A mixture of trans-3-(3-Methoxyphenyl)-2-propenenitrile (27.6 g, 173 mmol) and PtO2 (2.76 g) in 200 mL of EtOH and 30 mL of CHCl3 was shaken in a Parr apparatus under an atmosphere of 50-60 psi H2 overnight at RT. The reaction mixture was filtered through Celite and concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic layers were then dried over MgSO4, filtered and concentrated in vacuo to provide 24.2 g of the desired product as a yellow oil (85% yield). 1H NMR (CDCl3) δ 7.15-7.22 (m, 1H), 6.70-6.80 (m, 3H), 3.80 (s, 3H), 2.72 (t, J=6.0 Hz, 2H), 2.58-2.65 (m, 2H), 1.70-1.85 (m, 2H). The reaction mixture was filtered through Celite concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH The organic phase was separated the aqueous phase was extracted with CH2Cl2 (3×100 mL) The combined organic layers were then dried over MgSO4 filtered concentrated in vacuo