1,4-Dibromobutane → 1-(3-methoxyphenyl)pyrrolidine

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

Procedure

To a stirring solution of 3-methoxy-phenylamine (571 mg, 4.6 mmol) in anhydrous toluene (40 ml) was added 1,4-dibromo-butane (1.0 g, 4.6 mmol) and diisopropylethylamine (0.59 g, 4.6 mmol). The resulting solution was heated to reflux for 24 hours and then concentrated in vacuo. The crude material was purified by column chromatography over silica gel (silica gel 60, EM science, 5% EtOAc:hexanes) and the title compound was obtained as an oil (754 mg, 92%). MS(ES) m/e 178.4 ([M+H]+).