Hydrochloric Acid → 2-(Cyclohexylsulfanyl)ethan-1-amine--hydrogen chloride (1/1)

To a solution containing 30 parts of sodium methoxide and 198 parts of methanol, maintained at 25° under a nitrogen atmosphere, is added rapidly 39 parts of cyclohexyl mercaptan. 51 Parts of 2-bromoethylamine hydrobromide then is added portion wise while maintaining the temperature at 25-30°, and the reaction mixture is stirred for 30 minutes. Then the mixture is refluxed for 3 hours, and the solid which forms is separated by filtration and washed with methanol. Residual solvent is removed under reduced pressure to yield a solid which is diluted with water and extracted with ether. The ethereal extracts are dried over a molecular sieve and filtered. The solvent is removed under reduced pressure to afford an oil which is dissolved in anhydrous ether. That solution is cooled in an ice bath while slowly adding isopropanolic hydrochloric acid. The precipitate which forms is recovered by filtration, washed with ether and air dried to afford pure 2-(cyclohexylthio)ethylamine hydrochloride, melting at about 210°-211°.

1. temperaturemaintained at 25° under a nitrogen atmosphere
2. temperaturewhile maintaining the temperature at 25-30°
3. temperatureThen the mixture is refluxed for 3 hours
4. customthe solid which forms is separated by filtration
5. washwashed with methanol
6. customResidual solvent is removed under reduced pressure
7. customto yield a solid which
8. extractionextracted with ether
9. customThe ethereal extracts are dried over a molecular sieve
10. filtrationfiltered
11. customThe solvent is removed under reduced pressure
12. customto afford an oil which
13. temperatureThat solution is cooled in an ice bath
14. filtrationThe precipitate which forms is recovered by filtration
15. washwashed with ether and air
16. customdried

ORD record

ord-49cb2cc4242549ea850a927029b465d1

Source dataset

uspto-grants-1977_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04020079