Ammonia → HCID 69959201, compound

Participants

Reaction Steps

(1RS,3aRS)-1-(2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl)-piperidin-4-one (2.62 g, 9.7 mmol) was dissolved in acetic acid (12 ml). Aniline (0.97 ml, 10.6 mmol) and trimethylsilylcyanide (1.2 ml, 9.7 mmol) were added and the mixture was stirred for 3 h at RT. The reaction mixture was poured into cold ammonia solution (40 ml), extracted with methylene chloride (2×200 ml) and brine (150 ml). The combined organic layers were combined, dried with magnesium sulfate and concentrated. Crystallization from diethylether/hexane yielded (1RS,3aRS)-1-(2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl)-4-phenylamino-piperidine-4-carbonitrile (3.1 g, 86%) as a pale yellow solid, m.p. 142° C. and MS: m/e=372.4 (M+H+).

Provenance & Evidence