1,3-Benzodioxole-5-carbonyl chloride → (-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-3,4-methylenedioxybenzamide

HRID 1017618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1017618
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH2:15])=[CH:5][C:4]=1[O:16][CH3:17].[CH2:18]1[O:29][C:28]2[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][C:20]=2[O:19]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][C:4]1[CH:5]=[C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]3[O:29][CH2:18][O:19][C:20]=3[CH:21]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 14321190(-)-cis-1,2-Dimethoxy-4-(2-aminocyclohexyl)benzene2×

Produkt 1

HCID 54164802(-)-cis-n-[2-(3,4-Dimethoxyphenyl)cyclohexyl]-3,4-methylenedioxybenzamideAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4.0 g of (−)-cis-1,2-dimethoxy-4-(2-aminocyclohexyl)benzene (compound B2) are dissolved in 100 ml of methylene chloride and 5.0 ml of triethylamine. A solution of 3.8 g of 3,4-methylenedioxybenzoyl chloride in 50 ml of methylene chloride is added dropwise at RT and the mixture is extracted with 100 ml each of water, 2N hydrochloric acid, satd. sodium hydrogencarbonate solution and water again after stirring overnight. The organic phase is dried using sodium sulfate and concentrated. 6.2 g of the title compound are obtained.

Aufarbeitung

  1. extractionthe mixture is extracted with 100 ml each of water, 2N hydrochloric acid
  2. customThe organic phase is dried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e7f4af18d6804e93a2cc60f50f52e9c6
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479505B1

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