Dimethyl Sulfide → 2-Aminomethyl-4-(3-chloropropyl)pyridine

Reaction equation

B.CSC.[Cl:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]#[N:16])[CH:10]=1.CSC>O1CCCC1>[NH2:16][CH2:15][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][Cl:5])[CH:14]=[CH:13][N:12]=1

Participants

Procedure

A solution of borane-dimethylsulfide (0.83 ml, 7.7 mmol) in 7 ml of tetrahydrofuran is added slowly to a refluxing solution of 4-(3-chloropropyl)-2-cyanopyridine (1.24 g, 6.9 mmol) in 7 ml of tetrahydrofuran while dimethylsulfide simultaneously distills off. The mixture is refluxed for 15 minutes after the addition is complete, cooled to 30° and 6 ml of 6N hydrochloric acid is added. After hydrogen evolution ceases, the mixture is refluxed for 30 minutes, cooled to 0° and saturated with solid sodium carbonate before extracting with methylene chloride (4×50 ml). The organic extracts are dried over sodium sulfate and evaporated to yield an oil which is filtered through 10 g of silica gel (1:1 EtOAc-MeOH) to yield 2-aminomethyl-4-(3-chloropropyl)pyridine as a yellow oil; NMR (CDCl3) 3.55 (t, 2H), 4.20 (s, 2H).