Water → HCID 21473647, compound

Participants

Reaction Steps

1.016 g (0.0050 mol) of (1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-methanol were added to a suspension of 0.20 g (0.0050 mol) of NaH (60% in oil) in 10 ml of tetrahydrofuran and the mixture was stirred at room temperature for 30 minutes Then, 0.60 ml (0.0050 mol) of benzyl bromide was added and the mixture was stirred at room temperature for a further 2 hours. The reaction mixture was subsequently treated with water and extracted with diethyl ether. The organic phase was dried over MgSO4, concentrated and the residue was chromatographed on silica gel with hexane/ethyl acetate 9:1 to 3:1 as the eluent. 0.515 g (35%) of 1-benzyl-4-benzyloxymethyl-1,2,3,6-tetrahydropyridine was obtained as a yellow oil. MS (ISP): me/e=2.94 (C20H24NO+).

Provenance & Evidence