1-Benzyl-4-piperidone → 1-(Phenylmethyl)spiro[piperidine-4,2'(1'H)-quinazoline]-4'-amine dihydrochloride

Participants

Reaction Steps

A solution of 2-aminobenzamidine dihydrochloride (2.0 g, 9.6 mmol) and N-benzyl4-piperidone (2.1 ml, 11.5 mmol) in ethanol (40 ml) and HCl (1M in Et2O, 5 ml) was heated at 70° C. for 20 h. Evaporation and flash column chromatography on untreated alumina eluting with DCM/methanol (10:1) gave after trituration from ether a yellow solid, MS (+EI) 307 ([M+H]+), 1H NMR (d6 -DMSO) 9.99 (1H, s), 9.1 (1H, s), 8.5 (1H, s), 7.81 (1H, d), 7.53 (1H, s), 7.46 (1H, t), 7.2-7.4 (5H, m), 6.89 (1H, d), 6.79 (1H, dd), 3.52 (2H, s), 2.4-2.6 (4H, m), 1.91 (2H, m), 1.82 (2H, m).

Provenance & Evidence