Hydrochloric Acid → HCID 67263856, compound

Participants

Reaction Conditions

Reaction Steps

1-(5,5-Dimethyl-8-nitro-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-2-pyrrolidin-1-yl-ethanone (0.508 g, 0.00153 mol), 1.00 M of Borane-THF complex in tetrahydrofuran (7.7 mL; Acros) and anhydrous tetrahydrofuran (12.4 mL) were combined in a round bottom flask and heated to 70° C. for 6.5 hours. Concentrated HCl was added dropwise until gas evolution stopped. Solvent was removed under reduced pressure, then an additional 5 mL of conc. HCl was added until the mixture was pH 1. The reaction was heated at 100° C. for 1.5 hours. The reaction was removed from the heat and 10 N NaOH (6 mL) was added until the mixture was pH 7-8. Na2CO3 was added until the solution was pH 11. The solution was extracted twice into DCM, and the combined organic layers were dried with sodium sulfate, filtered and concentrated under reduced pressure to yield a crude brown oil, 5,5-Dimethyl-8-nitro-1-(2-pyrrolidin-1-yl-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine. LCMS: m/z=332.35 (M+H+).

Provenance & Evidence