Benzyltrimethylammonium hydroxide → 3-[3-[(3-Methylpyrrolidin-1-yl) methyl]phenoxy]propanamine

반응식

[CH3:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:3]1.[OH-].[CH2:16]([N+:23](C)(C)C)[C:17]1C=CC=C[CH:18]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(#N)C=C>[CH3:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:18][CH2:17][CH2:16][NH2:23])[CH2:3]1

참가 물질

실험 절차

28.7 g (0.15 mol) of 3-[(3-methylpyrrolidin-1-yl) methyl]phenol are heated under reflux together with 100 ml of acrylonitrile and 1.5 ml of 40% methanolic benzyltrimethylammonium hydroxide solution for 18 hours. The excess acrylonitrile is evaporated off under vacuum and the residue is taken up with ether, washed with 5% NaOH and reduced to the amine by reaction with 7.6 g (0.2 mol) of LiAlH4 in a manner analogous to Example 64 b. 14.9 g (40% of theoretical) of a pale yellow oil is obtained in a sufficiently pure form for subsequent reactions.