Reaktion #77756

Reaktionsgleichung

6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

N-allyl-methylamine

→

6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Ausbeute 74.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in Et2O
3. 3
   ExtraktionThe inorganic layer was extracted with Et2O
4. 4
   Waschenthe combined organic phases were washed with water
5. 5
   Trocknendried over Na2SO4
6. 6
   SonstigePurification by column chromatography on silica gel with CH2Cl2/MeOH 10:1

Vorschrift

5.0 g (13.0 mmol) 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester were treated with 3.66 g (51.5 mmol) N-allyl-methylamine in 100 ml DMF at 50° C. for 30 min. The mixture was concentrated in vacuo, dissolved in Et2O and water. The inorganic layer was extracted with Et2O, and the combined organic phases were washed with water and dried over Na2SO4. Purification by column chromatography on silica gel with CH2Cl2/MeOH 10:1 yielded 3.6 g (74%) 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as light yellow oil, MS: 375 (MH+).

Quelle