Hydrochloric Acid → 1-Cyclohexylpyrrolidin-3-ol

To 99 g. of cyclohexylamine at reflux temperature is added 115.5 g. of 1,4-dibromo-2-butanol at a rate which maintains reflux without external heating. The temperature of the reaction mixture is maintained at 130°-140° C. in an oil bath for two hours after addition is complete. Water (100 ml.) is added and this mixture is then acidified with concentrated hydrochloric acid, cooled and extracted with ether. The aqueous layer is made alkaline with 50% aqueous sodium hydroxide solution, saturated with solid potassium carbonate and extracted three times with chloroform. The combined chloroform extracts are dried over potassium carbonate, concentrated and the residue distilled in vacuo to give N-cyclohexyl-3-pyrrolidinol.

1. additionis added 115.5 g
2. temperatureThe temperature of the reaction mixture is maintained at 130°-140° C. in an oil bath for two hours
3. additionafter addition
4. temperaturecooled
5. extractionextracted with ether
6. extractionsaturated with solid potassium carbonate and extracted three times with chloroform
7. dry with materialThe combined chloroform extracts are dried over potassium carbonate
8. concentrationconcentrated
9. distillationthe residue distilled in vacuo

ORD record

ord-e65e6c09481b4ab8a6bf27fd7aff8d1c

Source dataset

uspto-grants-1977_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04005208