Benzene → HCID 22615398, compound

Participants

Reaction Steps

A solution of the piperidone (2.5 g, 11.4543 mmol), ethylene diamine (6.89 g, 114.543 mmol) and p-toluene sulphonic acid (0.105 g, 0.57272 mmol) in benzene (100 mL) was refluxed under a Dean-Stark trap until cessation of water azeotrope. The solvent was removed in vacuo , diluted with MeOH (50 mL) and treated with NaBH3CN (0.714 g, 11.4543 mmol) at room temperature (1 h). The solvent was removed in vacuo, diluted with DCM (50 mL) and saturated aqueous sodium bicarbonate (25 mL), partitioned, extracted with DCM (2×50 mL), washed with saturated aqueous sodium bicarbonate (2×25 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo and submitted to PCTLC (SiO2, 6 mm, 80/20/2 CHCl3—MeOH—NH4OH) affording the titled amine (67).

Provenance & Evidence