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1-Hydroxybenzotriazole → 4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1665582
Notes
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Reaction equation

HRID 1665582 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:30]([F:33])([F:32])[F:31])=[C:25]([CH:29]=1)[C:26]([OH:28])=O.CCN=C=NCCCN(C)C.Cl.[C:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>CN(C=O)C.O>[C:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][N:56]([C:26](=[O:28])[C:25]2[CH:29]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=2[C:30]([F:33])([F:32])[F:31])[CH2:55][CH2:54]1)=[O:52])([CH3:49])([CH3:47])[CH3:48]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6882945-Fluoro-2-(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57875800
4-(5-Fluoro-2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester
Yield 88.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (163 mg, 1.2 mmol) and DIEA (373 mg, 2.9 mmol) were added to a stirred solution of 5-fluoro-2-trifluoromethyl-benzoic acid (200 mg, 0.9 mmol) in DMF (1.0 mL) and the resulting mixture was cooled to 10° C. EDCI.HCl (231 mg, 1.2 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (197 mg, 1.0 mmol) were then added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and the product extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude residue, which was purified by column chromatography using silica gel 60-120 mesh (30% ethyl acetate in hexane) to afford 301 mg (83%) of 4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester, LCMS purity: 99.5%.

Workup

  1. additionwere then added
  2. extractionthe product extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude residue, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f5c8130923ba47fba1aac1ef268e607b
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08039463B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes