반응 #546847

반응 방정식

1-(pyrrolidino)-1-cyclohexene

dimethylamine hydrochloride

sodium iodide

triethylamine

chlorotrimethylsilane

2-chlorobenzaldehyde

→

2-[(2-chlorophenyl) dimethylaminomethyl]cyclohexanone

수율 68.0%

용매

hydrochloric acid

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued at RT for a further hour
4. 4
   온도The mixture was cooled again to 0° C. with an ice-bath
5. 5
   workup.STIRRINGstirring
6. 6
   workup.WAITwas continued at RT for two hours
7. 7
   온도while cooling with ice
8. 8
   workup.STIRRINGthe mixture was stirred for 10 minutes
9. 9
   세척washed twice with 300 ml ether each time
10. 10
    추출The mixture was extracted three times with 300 ml ether each time
11. 11
    건조the combined organic extracts were dried over sodium sulfate
12. 12
    여과filtered
13. 13
    농축concentrated on a rotary evaporator (500 to 10 mbar)
14. 14
    온도without heat

실험 절차

17.4 g (213 mmole) of freshly dried dimethylamine hydrochloride were added, while stirring, to 471 mg (469 mmole) sodium iodide solution (1 M in acetonitrile), which was cooled to 0° C. with an ice-bath; 60 ml (427 mmole) triethylamine and 60 ml (469 mmole) chlorotrimethylsilane were added dropwise, and the mixture was subsequently stirred at RT for one hour. While cooling with ice, 24 ml (213 mmole) 2-chlorobenzaldehyde were added, and stirring was continued at RT for a further hour. The mixture was cooled again to 0° C. with an ice-bath; 34 ml (213 mmole) 1-(pyrrolidino)-1-cyclohexene were added, and stirring was continued at RT for two hours. For working up, 300 ml half-concentrated hydrochloric acid were added to the mixture, while cooling with ice, and the mixture was stirred for 10 minutes, washed twice with 300 ml ether each time and rendered alkaline (pH approx. 9) with 770 ml dilute ammonia solution (5 vol. %). The mixture was extracted three times with 300 ml ether each time, and the combined organic extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar) without heat being supplied. 38.3 g 2-[(2-chlorophenyl) dimethylaminomethyl]cyclohexanone (68% of theoretical) were obtained in this manner.

출처