2-(Trifluoromethyl)benzoic acid → HCID 17683255, compound

HRID 1177864Notes

Reaction equation

HRID 1177864 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.[CH2:44]([N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C.CCCCCC.O>[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[C:11]([F:10])([F:22])[F:21])=[O:16])[CH2:53][CH2:52]1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

9

Reactant 5

HCID 98992-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 17683255HCID 17683255, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

DIPEA (13.6 mL, 78.90 mmol) was added drop wise to 2-trifluoromethyl-benzoic acid (5 g, 26.30 mmol) in DMF (20 mL). EDCI (12.6 g, 65.75 mmol) and HOBT (4.26 g, 31.56 mmol) were added consecutively and after 10 mins, 1-benzyl-piperazine (5.56 g, 31.56 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2 SO4 and concentrated under reduced pressure to afford 12.6 g of crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 30/70 EtOAc:hexane as the eluent) afforded 8.6 g (93% yield) of (4-benzyl-piperazin-1-yl)-(2-trifluoromethyl-phenyl)-methanone.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washwashed with brine
  3. customThe organic phase was dried over Na2 SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford 12.6 g of crude product
  6. customPurification by column chromatography (

Sources & evidence

ORD record
ord-b213a593b0144e19aa1f34d9dd679383
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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