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

HRID 912887Notes

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

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 (111 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

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

Sources & evidence

ORD record: ord-06b8b03b67ca43dd8e62875f1ded4b51
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026241B2

Reaction notes

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