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

HRID 49483
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49483
[CH2:1]([N:4]([CH3:22])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH2:17][CH2:16][CH2:15]2)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.Cl[C:33]([O:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)=[O:34]>C(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([O:35][C:33]([N:18]2[C:19]3[C:14](=[CH:13][C:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH:2]=[CH2:3])[CH3:22])=[CH:21][CH:20]=3)[CH2:15][CH2:16][CH2:17]2)=[O:34])=[CH:37][CH:38]=1
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Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 21966553Allyl-methyl-[6-(1,2,3,4-tetrahydro-quinolin-6-yloxy)-hexyl]-amine

Produkt 1

HCID 695147796-[6-(Allyl-methyl-amino)-hexyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl esterAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in ether
  3. extractionThe inorganic phase was extracted with ether
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-19aebbc61a9b4725be1830a1627da180
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06706751B2

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