Reaktion #77776

Reaktionsgleichung

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

Ausbeute 85.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe solution was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was redissolved in ether
3. 3
   workup.ADDITION2M NaOH was added
4. 4
   Extraktionthe inorganic phase was extracted with ether
5. 5
   WaschenThe combined organic phases were washed with water
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigeevaporated

Vorschrift

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+).

Quelle