Cyclohexanecarboxaldehyde → HCID 67339402, compound

Participants

Reaction Steps

To a solution of N-(2-aminoethyl)-1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide E13 (50 mg, 0.16 mmol) in MeOH (5 mL) was added cyclohexanecarbaldehyde (19 μL, 0.16 mmol). After stirring for 2 h, sodium cyanoborohydride (20 mg, 0.32 mmol) was added and the mixture was stirred for a further 16 h. The solvent was removed under reduced pressure, the residue was dissolved in EtOAc (20 mL), washed with a saturated solution of sodium hydrogencarbonate (25 mL), brine (25 mL), dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1) to furnish the title compound as a white solid (15 mg, 23%), m.p. 174-177° C.; umax (CHCl3)/cm−1 2932, 2856, 1665, 1558, 1457, 1236, 1146, 1037; m/z (ESI) C20H31Cl22N4O requires 413.1869, found [M+H]+ 413.1875.

Provenance & Evidence