Pyrrolidine → HCID 22709049, compound

212 g of 4-propylcyclohexanone and 200 ml of pyrrolidine was dissolved in 600 ml of toluene, and the mixture was heated with stirring for 3 hours, and any azeotropically distilled water was removed. Excess pyrrolidine was then removed by azeotropic distillation with toluene, to obtain 1-(4-propylcyclohexa-1-en-1-yl)-pyrrolidine. The crude product was cooled, as is, to room temperature, a further 800 ml of toluene was added, the mixture was cooled in a water bath, and 120 ml of methyl vinyl ketone was added dropwise over a period of 1 hour at a temperature of 25° C. or lower. Following completion of the addition, the mixture was immediately heated and refluxed for 20 hours. The solution was then cooled to room temperature, a buffer solution of pH 5 prepared from 63 g of sodium acetate, 120 ml of acetic acid and 140 ml of water was added, and the reflux was continued for a further 4 hours. After the solution had been cooled to room temperature, the organic layer was separated and washed with water and a saturated aqueous solution of sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, and the solvent removed by evaporation to obtain 320 g of a crude product of 6-propyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one.

1. temperaturethe mixture was heated
2. customany azeotropically distilled water was removed
3. customExcess pyrrolidine was then removed by azeotropic distillation with toluene

ORD record

ord-14824dcd0caa4ca4ba83637caaf1f06f

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06746728B1