3-(3,4,5-Trimethoxyphenyl)acrylic acid → 2-Propenoyl chloride, 3-(3,4,5-trimethoxyphenyl)-, (2E)-

0.86 gram (3.62 millimoles) of 3,4,5-trimethoxycinnamic acid and 16.3 grams (137 millimoles) of thionyl chloride were heated together at reflux temperature for 45 minutes to obtain 3,4,5-trimethoxycinnamoyl chloride. The reaction mixture was subjected to reduced pressure to vaporize excess thionyl chloride and to recover the acid chloride as residue. The acid chloride was purified by repeated dissolution in benzene and vaporizing the volatile matter. The purified acid chloride residue was dissolved in 15 milliliters of dry methylene chloride and the solution cooled to 0° C. To the solution was added a solution of 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine and triethylamine in 15 milliliters of methylene chloride. The resulting mixture was allowed to warm to room temperature and then stirred overnight. As the end of this time, the mixture was diluted with methylene chloride and washed successively with 2N hydrochloric acid, aqueous sodium bicarbonate and brine and thereafter dried. The dried solution was subject to reduced pressure to remove the solvent and to obtain 1.84 grams of 4-(5H-dibenzo-[a,d]cyclohepten-5-yl) 1-(3,4,5-trimethoxyphenyl)prop-2-enoyl)piperidine as a light brown foamy solid. The latter was flash chromatographed on 80 grams of silica gel employing 40/60 ethyl acetate/hexane as eluant to obtain 1.06 grams of the product as an oil.

1. temperatureat reflux temperature for 45 minutes

ORD 기록

ord-e16c6f1f19804f39885c95146347744c

출처 데이터셋

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04758577