Benzo-1,3-dioxole-5-methylamine → 4-[(Benzo[1.3]dioxol-5-ylmethyl)-amino]-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

Participants

Reaction Steps

Piperonylamine (0.030 ml, 0.24 mmol) and sodium triacetoxyborohydride (0.08 g, 0.377 mmol) were added to a solution of 4-hydroxy-4-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanone (0.06 g, 0.2 mmol) in dichloromethane (1 ml). The reaction mixture was stirred overnight and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane:MeOH 9/1 and then dichloromethane:MeOH 9/1 and 2% triethylamine).

Provenance & Evidence