Hydrogen chloride-ethyl acetate → 1-(2,4-Dimethylphenyl)-[1,4]diazepane hydrochloride

HRID 2411224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2411224
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23].C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:23].[CH3:22][C:16]1[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=1[N:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Komponenten

4

Edukt 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 673808924-(2,4-Dimethylphenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 673808831-(2,4-Dimethylphenyl)-[1,4]diazepane hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a mixture of 1-bromo-2,4-dimethylbenzene (1.85 g), 1-Boc-[1,4]diazepane (2 g), palladium(II) acetate (0.12 g), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.31 g) and sodium tert-butoxide (1.34 g) was added toluene (35 mL), and the mixture was stirred with heating under reflux for 9 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give 4-(2,4-dimethylphenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (2.16 g). The obtained 4-(2,4-dimethylphenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (2.16 g) was dissolved in chloroform (17 mL), 4N hydrogen chloride/ethyl acetate solution (6.9 mL) was added, and the mixture was stirred at room temperature overnight. The solvent was evaporated from the reaction mixture to give the title compound (1.74 g).

Aufarbeitung

  1. customThe solvent was evaporated from the reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-2ffa92ca622542e5a1c43150cde7d769
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816079B2

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