Diisopropylethylamine → 4-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

HRID 730827Notes

Reaction equation

HRID 730827 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[F:16][C:15]([F:18])([F:17])[C:14]1[C:9]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 471744384-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of piperazin-2-one (4.85 g, 48.47 mmol, Avocado Research), 2-chloro-3-trifluoromethyl-pyridine (8.8 g, 48.47 mmol, TCI America) and diisopropylethylamine (11 mL, 58.16 mmol, Aldrich) in DMSO (160 mL) was heated at 120° C. for 16 h. The mixture was cooled to room temperature, diluted with H2O (500 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with dichloromethane/MeOH (15:1) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 206 (M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane/MeOH (15:1)

Sources & evidence

ORD record
ord-2173b642f10942b68982dc1ad14f91f5
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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