2-(Trifluoromethyl)benzoyl chloride → HCID 44203151, compound

HRID 1985635Notes

Reaction equation

HRID 1985635 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>ClCCl>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([F:23])([F:34])[F:35])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 44203151HCID 44203151, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-Boc-piperazine (1.96 g, 10.5 mmol) and diisopropylethylamine (2.714 g, 21 mmol, 3.63 mL) in dichloromethane (50 mL) was added 2-trifluoromethylbenzoyl chloride (2.086 g, 10.0 mmol) dropwise. The resulting mixture was stirred at room temperature for 1 minutes and then quenched with water (25 mL). The organic phase was separated and washed with H2O, brine, dried over MgSO4 and then concentrated in vacuo to afford product 4-(2-trifluoromethylbenzoyl)-piperazine-1-carboxylic acid tert-butyl ester as pale yellow solid. Yield 95%, 3.575 g.

Workup

  1. customquenched with water (25 mL)
  2. customThe organic phase was separated
  3. washwashed with H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-392b1acef0b2438ea9ccc186cf8f58d3
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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