Benzylamine → HCID 21104663, compound

Participants

Reaction Steps

Benzylamine (0.135 ml, 1.24 mmol) and sodium triacetoxyborohydride (0.315 g, 1.55 mmol) were added to a solution of 4-[2-(6-methoxy-quinolin-4-yl)-ethyl]-cyclohexanone (Example 26.e) (0.35 g, 1.23 mmol) in dichloroethane (8 ml). The reaction mixture was stirred for 2 hours. 3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbaldehyde (0.230 g, 1.3 mmol), THF (4 ml and sodium triacetoxyborohydride (0.315 g, 1.55 mmol) was added. The reaction mixture was stirred overnight and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 10 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 19/1).

Provenance & Evidence