Sodium Iodide → N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride

To a solution of 5,5-diphenyl-2-cyclopenten-1-ol (0.30 g) in acetone were added methanesulfonyl chloride (0.12 ml) and triethylamine (0.21 ml) at 1° C. to 3° C. After being stirred for 15 minutes sodium iodide (0.23 g) was added thereto and the mixture was stirred for 10 minutes. To the mixture was added t-butylamine (2.67 ml) at -1° C. to 2° C. and the mixture was stirred at room temperature overnight. Cold water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was dissolved in ethyl acetate. To the solution was added 3N hydrochloric acid (1 ml) with cooling in an ice bath, and the mixture was stirred for 30 minutes. The resulting precipitates were collected by filtration, washed with water, ethyl acetate successively and dried to give N-t-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride (0.31 g).

1. additionwas added
2. stirringthe mixture was stirred at room temperature overnight
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with brine
5. dry with materialdried over sodium sulfate
6. customevaporated in vacuo
7. dissolutionThe residue was dissolved in ethyl acetate
8. additionTo the solution was added 3N hydrochloric acid (1 ml)
9. temperaturewith cooling in an ice bath
10. stirringthe mixture was stirred for 30 minutes
11. customThe resulting precipitates
12. filtrationwere collected by filtration
13. washwashed with water, ethyl acetate successively
14. customdried

ORD record

ord-fa080201e4fc4734978ba59a17926e99

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05256824