Dichloromethane → N,N-diethyl-4-[[4-(2-thiophenylmethyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide Dihydrochloride

Participants

Reaction Steps

To a solution of compound 1 (0.99 mmol) in methylene chloride (10 ml) was added 2-thiophenecarboxaldehyde (190 ul; 1.98 mmol) followed by acetic acid (0.1 ml; 1%). The mixture was stirred 30 minutes then sodium triacetoxyborohydride (0.63 g; 2.97 mmol) was added and the reaction mixture stirred overnight. The reaction mixture was neutralized with sodium hydroxide 2N and extracted with methylene chloride (3×). The combined methylene chloride extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by reverse phase using 10%-30% CH3CN/H2O (TFA as the buffer) gave 115 mg of desired product (TFA salt).

Provenance & Evidence