Ethanolamine → 4-[3-(2-Hydroxyethylamino)propyl]benzonitrile

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19]([CH2:21][NH2:22])[OH:20]>C(#N)C>[OH:20][CH2:19][CH2:21][NH:22][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

Procedure

To a solution 4-(3-bromopropyl)benzonitrile (8 g, 0.0357 mol; see step (iv) above) in dry acetonitrile (150 mL) were added anhydrous K2CO3 (7.4 g, 0.0535 mol) and ethanolamine (10.9 g, 0.179 mol). The resulting reaction mixture was then stirred overnight at room temperature, after which it was filtered and concentrated. The crude product thus obtained was purified by column chromatography over silica gel, using methanol in chloroform as eluent, to yield 4.2 g (57.5%) of the sub-title compound as a pale yellow solid.