Reaktion #77761

Reaktionsgleichung

Allyl-methyl-[6-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-hexyl]-amine

Huenig's base

4-chlorophenyl chloroformate

→

6-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

Ausbeute 50.3%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ether
3. 3
   ExtraktionThe inorganic phase was extracted with ether
4. 4
   Waschenthe combined organic phases were washed with water
5. 5
   Trocknendried over Na2SO4

Vorschrift

To 60.4 mg (0.2 mmol) Allyl-methyl-[6-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-hexyl]-amine in 2 ml CH2Cl2 1 drop of Huenig's base and 57 mg (0.3 mmol) 4-chlorophenyl chloroformate in 1 ml CH2Cl2 were added. The solution was stirred at RT for 30 min, was concentrated and the residue was dissolved in ether and a saturated aqueous solution of NaHCO3. The inorganic phase was extracted with ether and the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1 yielded 46 mg (50%) 6-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless oil, MS: 457 (MH+, 1Cl).

Quelle