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Hydrochloric Acid → 1-(4-Phenyl-1,3-thiazol-2-yl)piperazine

HRID 2262988
Notes
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Reaction equation

HRID 2262988 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(OCC)C>C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68777857Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate

Product 1

HCID 7124681-(4-Phenyl-1,3-thiazol-2-yl)piperazineYield 80.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

tert-Butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate (691 mg, 2.00 mmol) was dissolved in ethyl acetate (50 ml), and a solution of 4 N hydrogen chloride in ethyl acetate (11 ml) was added thereto, followed by stirring at room temperature for 1 hour and half. Diethyl ether (20 ml) was poured to the reaction mixture, and a solid was separated by filtration, which was dissolved in an aqueous 1 N sodium hydroxide solution (7 ml). Water was poured to the reaction mixture, and the resulting solution was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 396 mg (80.8%) of the desired product as an oil.

Workup

  1. customa solid was separated by filtration, which
  2. dissolutionwas dissolved in an aqueous 1 N sodium hydroxide solution (7 ml)
  3. additionWater was poured to the reaction mixture
  4. extractionthe resulting solution was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7589fb7cb62749a891620c5bbd18c510
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes