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Dimethylformamide → Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate

HRID 2262896
Notes
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Reaction equation

HRID 2262896 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:7]1([C:5]2[N:6]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]3)[S:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27613592-Chloro-4-phenylthiazole

Product 1

HCID 68777857Tert-butyl 4-(4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-4-phenyl-1,3-thiazole (1.16 g, 5.92 mmol), 1-(tert-butoxycarbonyl)-piperazine (3.30 g, 17.8 mmol), potassium carbonate (817 mg, 5.92 mmol) and N,N-dimethylformamide (20 ml) was stirred at 120° C. for 2 hours, poured to water, which was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate to yield 1.43 g (70.1%) of the desired product.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-f6708f12a54e4d34a6c9fa1c793c85af
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851473B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes