반응 #424788

반응 방정식

cyclopropylamine

2-bromobenzyl alcohol

triethylamine

methanesulfonyl chloride

→

title compound

N-[(2-Bromophenyl)methyl]cyclopropanamine

용매

THF

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.WAITAfter another 18 h
3. 3
   기타quenched with 1 N aq. NaOH
4. 4
   추출The organic extract
5. 5
   기타was separated
6. 6
   세척washed with brine
7. 7
   건조dried over Na2SO4
8. 8
   여과filtered
9. 9
   농축the filtrate concentrated in vacuo
10. 10
    기타Purification of the crude product
11. 11
    기타thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc)

실험 절차

To a THF solution (0.15 M) of 2-bromobenzyl alcohol (1 eq.) was added triethylamine (1.6 eq.). The reaction mixture was cooled to 0° C. before methanesulfonyl chloride (1.3 eq.) was added dropwise. The resulting solution was then allowed to warm slowly to RT. After 1.5 h, cyclopropylamine (5 eq.) was added to the now cloudy suspension. After another 18 h, the reaction mixture was diluted with ether and quenched with 1 N aq. NaOH. The organic extract was separated, washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

출처