Potassium Carbonate → 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 49475

Reaktionsgleichung

Reaktionsgleichung von HRID 49475
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([NH:28][CH3:29])[CH:26]=[CH2:27].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:28]([CH2:25][CH:26]=[CH2:27])[CH3:29])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 69391N-MethylallylamineHCID 695149026-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 695146996-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.5 g (3.75 mmol) 6-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester were treated with 355 mg (5 mmol) N-allyl-methylamine and 830 mg (6 mmol) K2CO3 (powdered) in 8 ml DMF at 60° C. for 3 h. The mixture was concentrated in vacuo, dissolved in acetone and filtered. The filtrate was concentrated and purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 to yield 1.05 g (72%) 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as colorless oil, MS: 389 (MH+).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutiondissolved in acetone
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica gel with CH2Cl2/MeOH 19:1

Quellen und Nachweise

ORD-Eintrag
ord-61cd16c352fa472590d986d03d2eee59
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706751B2

Verknüpfte Notizen

Wird geladen…