Triethylamine → HCID 19079064, compound

Participants

Reaction Conditions

Reaction Steps

Dissolved N-[2-(5-ethoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)ethyl]-N-methylamine (150 mg, 0.508 mmol) in 5 mL of dry dichloromethane. Cooled to 0° C. under a nitrogen atmosphere, and added triethylamine (0.14 mL, 0.10 g, 1.0 mmol) and then methanesulfonyl chloride (0.06 mL, 0.089 g, 0.76 mmol) dropwise via syringe. Stirred at 0° C. for 90 mins. Added water, and extracted with dichloromethane. Washed the combined organic extracts with sodium phosphate monobasic, 1N NaOH, and then saturated NaCl. Dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography eluting with 9:1 hexane:ethyl acetate. Combined appropriate fractions, and evaporated to solid. Recrystallized from ethyl acetate-hexane to give 92 mg (48% yield) of N-[2-(5-ethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptenyl)ethyl]-N-methyl-methanesulfonamide as a white, solid.

Provenance & Evidence