Acetic Acid → HCID 68161673, compound

Participants

Reaction Steps

A solution of 4-[(2R,4S)-1-acetyl-2-ethyl-4-(phenylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzaldehyde (for a preparation see intermediate 92) (50 mg, 0.125 mmol), piperidine (0.019 mL, 0.188 mmol) and acetic acid (0.014 mL, 0.251 mmol) in dichloromethane (DCM) (4 mL) was stirred at room temperature under nitrogen for 30 min before being treated with sodium triacetoxyborohydride (34.6 mg, 0.163 mmol) portionwise. The resulting mixture was stirred at room temperature for 72 h then was partitioned between DCM (10 mL) and a saturated NaHCO3 aqueous solution (10 mL). The layers were separated and the organic phase was dried using a hydrophobic frit then concentrated in vacuo. Purification of the residue by MDAP (modifier: formic acid) gave (cis)-1-acetyl-2-ethyl-N-phenyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine formate salt (14.8 mg, 0.029 mmol, 23%).

Provenance & Evidence