Diisopropylcarbodiimide → HCID 57875821, compound

HRID 1665589Notes

Reaction equation

HRID 1665589 reaction equation
CC(C)N=C=NC(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[C:14]([OH:16])=O.[CH2:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([N:29]1[CH2:34][CH2:33][N:32]([C:14]([C:13]2[CH:17]=[C:18]([F:21])[C:19]([F:20])=[C:11]([F:10])[CH:12]=2)=[O:16])[CH2:31][CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 759941-BenzylpiperazineHCID 8531543,4,5-Trifluorobenzoic acid

Product 1

HCID 57875821HCID 57875821, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIC (1.34 g, 10.2 mmol) was added drop wise to a stirred solution of 3,4,5-trifluoro benzoic acid (1.5 g, 8.5 mmol) in THF (10 mL) and the resulting mixture was maintained for 30 minutes at room temperature. Mono benzyl piperazine (1.64 g, 9.35 mmol) was then added and the mixture heated to reflux at 70° C. overnight, under an atmosphere of nitrogen. The resulting solid precipitate was filtered and the filtrate was washed with water and evaporated. The residue was purified by column chromatography using silica gel 60-120 mesh (12% ethyl acetate in hexane) to afford 1.7 g (60%) of (4-benzyl-piperazin-1-yl)-(3,4,5-trifluoro-phenyl)-methanone. 1H NMR: (CDCl3): δ 7.32 (m, 5H), 7.06 (t, 2H), 3.75 (bs, 2H), 3.54 (s, 2H), 3.44 (bs, 2H), 2.46 (bs, 4H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux at 70° C. overnight, under an atmosphere of nitrogen
  3. filtrationThe resulting solid precipitate was filtered
  4. washthe filtrate was washed with water
  5. customevaporated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a1fcbd66b5a54b9f874dd5c85b9cea4e
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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