Hydrochloric Acid → HCID 59161276, compound

Participants

Reaction Steps

Mix 6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine.HCl (Preparation 51) (200 mg, 0.49 mmol), N,N-dimethylcarbamoyl chloride (54 μL, 63 mg, 0.59 mmol), triethylamine (205 μL, 149 mg, 1.47 mmol), CH2Cl2 (6 mL), and N-methylpyrrolidinone (2 mL). Stir at room temperature for 18 h, then add more N,N-dimethylcarbamoyl chloride (54 μL, 63 mg, 0.59 mmol). Stir at room temperature for 60 h, then evaporate the solvents. Dilute the residue with EtOAc (80 mL) and wash the organic solution with HCl (<1N in water, 40 mL) and aqueous NaHCO3. Dry (MgSO4), filter, and concentrate the organic portion to obtain 308 mg crude product as a brown oil. Purify on silica gel (12 g), eluting with 80-100% EtOAc/hexanes to afford 164 mg (75%) of the title compound as a white foam. MS (ES): 444, 446 (M+1); HPLC: Rt=3.27 min, (92%).

Provenance & Evidence