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

HRID 1820624Notes

Reaction equation

HRID 1820624 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-06c40a600d0f4c52b4b3e7e73f64a2ee
Source dataset
uspto-grants-2009_10
Patent number
US07605161B2

Reaction notes

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