Triethylamine → 1H-1-Benzazepine

Participants

Reaction Steps

To a stirred solution of 7-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine (0.37 g) and triethylamine (0.3 mL) in DCM (5 mL), at 0° C., trifluoroacetic anhydride (0.26 mL) was added dropwise. The ice bath was removed and the stirring continued for 4 h after which time aqueous saturated NaHCO3 (10 mL) was added, the reaction mixture was extracted twice with diethyl ether (10 mL), the organic phase dried over Na2SO4 and evaporated under reduced pressure to give the correspondent N-trifluoacetyl benzazepine derivative in 0.5 g yield. This product (0.11g) was dissolved in DMF (1 mL) and N-chlorosuccinimide (47 mg) was added, the reaction was warmed to 50° C. and stirred for 1 h. Then the reaction mixture was allowed to reach RT, water was added (4 mL), the mixture was extracted twice with ethyl ether (5 mL), the organic phase dried over Na2SO4 and evaporated under reduced pressure. The crude product so obtained was dissolved in MeOH (10 mL) and a solution of K2CO3 (0.36 g) in water (10 mL) was added, then the mixture was warmed to 55° C. and stirred for 2 h. The reaction mixture was concentrated under reduced pressure, extracted twice with DCM (10 mL), the organic phase dried over Na2SO4 and the solvent evaporated under reduced pressure to give the title compound (0.17 g) that was used as such.

Provenance & Evidence