Hydrochloric Acid → 1-[4-(2,3-Difluorophenyl)-1,3-thiazol-2-yl]piperazine hydrochloride

HRID 2263262Notes

Reaction equation

HRID 2263262 reaction equation
[ClH:1].[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[S:13][CH:14]=1.CCCCCC>C(OCC)(=O)C>[ClH:1].[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[N:11]=[C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[S:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 68781293Tert-butyl 4-[4-(2,3-difluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate

Product 1

HCID 687762881-[4-(2,3-Difluorophenyl)-1,3-thiazol-2-yl]piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A 4 N solution (50 ml) of hydrogen chloride in ethyl acetate was added to a solution of tert-butyl 4-[4-(2,3-difluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxylate (4.20 g, 11.0 mmol) in ethyl acetate (100 ml), and the mixture was stirred at room temperature for 14 hours. Hexane was added to the reaction mixture, and crystals were collected by filtration to give 1-[4-(2,3-difluorophenyl)-1,3-thiazol-2-yl]piperazine hydrochloride. The hydrochloride was dissolved in water, neutralized with a 1 N sodium hydroxide aqueous solution, and extracted with chloroform. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give 1.76 g (56.8%) of the desired product as a solid.

Workup

  1. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-dc32fcfb544e4a39b5e700b7d2f522cf
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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