Aluminium lithium hydride → 3-(Aminomethyl)-1-benzylpiperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-benzyl-3-cyano-4-hydroxypiperidine (2.3 g, 10.64 mmole) and lithium aluminum hydride (0.6 g, 15.97 mmole) in dry tetrahydrofuran (50 ml) was refluxed for 2 hr. The reaction mixture was cooled at 5° C. and quenched with water, aqueous NaOH (10%) and filtered. Filtrate was concentrated to dryness to afford crude 3-aminomethyl-1-benzyl-4-hydroxypiperidine. Yield 2.1 g (89.6%) C13H20N2O, m/z 221 (M+1), PMR (CDCl3): 1.1-1.9 (3H, m, H3 & H5), 2.1 (1H, m, H6), 2.82 (2H, m, H2), 3.4-3.96 (3H, m, H6 & CH2NH2), 4.16 (1H, m, H4), 4.84 (2H, s, N—CH2Ar), 7.34 (5H, m, ArH).

Provenance & Evidence