2-(Trifluoromethyl)benzoic acid → HCID 44203151, compound

HRID 1178041Notes

Reaction equation

HRID 1178041 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:44]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]>CN(C=O)C.O>[C:47]([O:46][C:44]([N:51]1[CH2:56][CH2:55][N:54]([C:14](=[O:16])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]([F:10])([F:22])[F:21])[CH2:53][CH2:52]1)=[O:45])([CH3:50])([CH3:48])[CH3:49]

Participants

8

Reactant 5

HCID 98992-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 44203151HCID 44203151, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (5.7 g, 44.30 mmol) was added drop wise to 2-trifluoromethyl benzoic acid (3.36 g, 17.72 mmol) in DMF (25 mL). EDCI (7.07 gm, 36.91 mmol) and HOBT (2.39 g, 17.72 mmol) were added consecutively and, after 15 minutes, N-Boc piperazine (2.75 g, 14.77 mmoles). The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 30:70 EtOAc:hexane as eluent) afforded 4-(2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester in 39% yield.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification

Sources & evidence

ORD record
ord-8e688b55f6074dfc99c1105a2219fc86
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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