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

HRID 1804035Notes

Reaction equation

HRID 1804035 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1-bromo-2,4-dimethylbenzene (1.85 g) were added 1-BOC-1,4]diazepane (2 g), palladium (II) acetate (0.115 g), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.31 g), sodium tert-butoxide (1.34 g) and toluene (35 mL), and the mixture was refluxed 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 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). To 4-(2,4-dimethylphenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (2.16 g) were added 4N hydrogen chloride/ethyl acetate (6.9 mL) and chloroform (17 mL), and the mixture was stirred at room temperature overnight. The solvent was evaporated to give the title compound (1.74 g).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-845ccd21ee304c4cadc6402690ab41fa
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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