Sodium cyanoborohydride → HCID 18665737, compound

Participants

Reaction Steps

1-(2,2-Diphenylethyl)-3(S)-piperidine carboxaldehyde (0.575 g, 1.96 mmol),3-(4-cyanobenzyl) histamine dihydrochloride (0.388 g, 1.30 mmol), and NaCNBH3 (0.123 g, 1.96 mmol) were dissolved in MeOH (15 mL) and stirred at ambient temperature overnight. The solution was concentrated and the residue taken up in EtOAc, washed with sat. NaHCO3 solution, H2O, and brine. The organics were dried, concentrated, and chromatographed (0-4% MeOH/CH2Cl2 /NH4OH) to give the title compound which was isolated as a tris HCl salt. 1H NMR (CD3OD); δ9.05 (s, 1H), 7.81 (d, 2H, J=8 Hz), 7.68 (s, 1H), 7.54 (d, 2H, J=8 Hz), 7.49-7.25 (m, 10H), 5.67 (s, 2H), 4.76-7.74 (m, 1H), 4.05-3.88 (m, 3H), 3.54-3.47 (m, 1H), 3.33-3.30 (m, 1H), 3.19-3.15 (m, 2H), 3.02-3.00 (m, 2H), 2.92-2.90 (m, 2H), 2.42 (br s, 1H), 1.99-1.91 (m, 2H), 1.82-1.78 (m, 1H), 1.31-1.28 (m, 2H).

Provenance & Evidence