Ethyl Acetate → 1-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

HRID 1804011Notes

Reaction equation

HRID 1804011 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:22].C(OCC)(=O)C.C(OCC)(=O)C>C(Cl)(Cl)Cl>[ClH:22].[CH3:20][C:19]1[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=[C:17]([CH3:21])[CH:18]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 673812824-(3,5-Dimethylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (25 g), methylboronic acid (8.4 g), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (1:1)(2.9 g) and potassium fluoride (16 g) was added tetrahydrofuran (140 mL), and the mixture was refluxed for 8 hr. After cooling, 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 (hexane:ethyl acetate) to give 4-(3,5-dimethylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (16 g). 4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (16 g) was dissolved in chloroform (100 mL), 4N hydrogen chloride/ethyl acetate (50 mL) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added, and the mixture was filtered to give the title compound (10 g).

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-97ee8c4ab41546cc9bd570261fd9da06
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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