Benzaldehyde → 4-Benzylamino-1-Butanol

Participants

Reaction Steps

Dissolve diaminooctane (10.8 g, 0.075) in methylene chloride (200 mL), methanol (100 mL) with di-t-butyldicarbonate (32.7 g, 0.156 mol). Stir the reaction overnight. Concentrate the reaction under vacuum and crystallize the residue from hexane to provide N, N'-bis(t-butoxycarbonyl)-1,8-octanediamine (20.2 g), mp 96-97° C. Combine 4-amino-butan-1-ol (8.9 g, 0.1 mol), benzaldehyde (10.6 g, 0.1 mol), ethanol (100 mL) and PtO2 (0.3 g) and hydrogenate at 45 lbs./sq. in. until hydrogen is no longer taken up. Filter the reaction and concentrate the filtrate under vacuum to provide 4-[[(phenyl)methyl]amino]-butan-1-ol (17.7 g), Rf =0.70 eluting with 10% conc. NH3 /methanol.

Provenance & Evidence