Hydrochloric Acid → HCID 68834821, compound

Participants

Reaction Steps

6 ml of 1 N sodium hydroxide and 18 ml of ethanol were added to 331 mg (1.0 mmol) of methyl 4-[(1-t-butoxycarbonylpiperidine-4-ylidene)methyl]benzoate, and they were stirred for 18 hours. The reaction liquid was acidified with 1 N hydrochloric acid. After the extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated. 5 ml of dimethylformamide, 0.22 ml (2.0 mmol) of N-methylmorpholine and 0.10 ml (1.0 mmol) of ethyl chloroformate were added to the residue under cooling with ice, and they were stirred for 30 minutes. 243 mg (1.0 mmol) of 3-(2-aminoethoxy)benzonitrile hydrobromide was added to the resultant mixture at that temperature. The temperature was elevated to room temperature, and they were stirred for one hour. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Provenance & Evidence