Diisopropylethylamine → HCID 178483793, compound

Participants

Reaction Steps

To 150 mg (0.55 mmol) of trans-N-(2-dimethylamino-ethyl)-N-methyl-2-(4-methylamino-cyclohexyloxy)-acetamide in 4 mL of CH2Cl2 were added 0.14 mL (0.8 mmol, 1.5 eq) of N,N-diisopropylethylamine followed by 0.08 mL (0.58 mmol, 1.1 eq) of 4-bromophenyl chloroformate. The mixture was stirred at RT for 2 h, and the solution was added to a mixture of NaHCO3 solution and CH2Cl2. The phases were separated and the inorganic one was extracted with CH2Cl2. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with CH2Cl2:MeOH 9:1 yielded 174 mg (67%) of trans-(4-{[(2-dimethylamino-ethyl)-methyl-carbamoyl]-methoxy}-cyclohexyl)-methyl-carbamic acid 4-bromo-phenyl ester as colorless oil, MS: 470 (MH+,1Br).

Provenance & Evidence