반응 #77776

반응 방정식

5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

N-allylmethylamine

DMF

→

5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

수율 85.0%

반응 조건

후처리

1. 1
   농축The solution was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was redissolved in ether
3. 3
   workup.ADDITION2M NaOH was added
4. 4
   추출the inorganic phase was extracted with ether
5. 5
   세척The combined organic phases were washed with water
6. 6
   건조dried over Na2SO4
7. 7
   기타evaporated

실험 절차

8.8 g (24 mmol) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 10 ml DMF were treated with 7.11 g (100 mmol) N-allylmethylamine at 50° C. for 4 h. The solution was concentrated in vacuo and the residue was redissolved in ether and water. 2M NaOH was added and the inorganic phase was extracted with ether. The combined organic phases were washed with water, dried over Na2SO4 and evaporated. Column chromatography with a gradient of CH2Cl2/MeOH 19:1 to 9:1 yielded 7.4 g (85%) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless oil, MS: 361 (MH+).

출처