2-(Trifluoromethyl)benzoyl chloride → HCID 66906079, compound

HRID 1689842Notes

Reaction equation

HRID 1689842 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[N:21][CH:22]=1)([O-:16])=[O:15].C(N(C(C)C)CC)(C)C>ClCCl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][N:26]([C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=3[C:2]([F:13])([F:12])[F:1])=[O:6])[CH2:27][CH2:28]2)=[N:21][CH:22]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 29287991-(5-Nitropyridin-2-yl)piperazine

Product 1

HCID 66906079HCID 66906079, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2-(Trifluoromethyl)benzoyl chloride (2.0 mL, 11.0 mmol) was added slowly to a solution of 1-(5-nitropyridin-2-yl)piperazine (2.0 g, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol) in dichloromethane (15 mL) at 0° C. under argon. The mixture was then stirred at 25° C. for 2 h. The reaction was quenched with H2O. The aqueous phase was extracted with ethyl acetate. The organic phase was washed with saturated NaCl and dried over anhydrous MgSO4. The organic phase was concentrated and then purified by column chromatography to yield [4-(5-nitropyridin-2-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone as a yellow solid (1.55 g, 41% yield). MS (ES+) m/z 381.1 (M+1).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated NaCl
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationThe organic phase was concentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-ca2a8914d4bb4131a51f4e950d3140a5
Source dataset
uspto-grants-2012_04
Patent number
US08153636B2

Reaction notes

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