Tetrahydrofuran → HCID 23024319, compound

HRID 915915Notes

Reaction equation

O1CCCC1.[F:6][C:7]1[CH:16]=[C:15](F)[C:14]([F:18])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:15]2[C:14]([F:18])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([F:6])[CH:16]=2)[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 30 ml tetrahydrofuran solution of 4.25 g (22.35 mmol) of methyl 2,4,5-trifluorobenzoate, 3.89 ml (22.35 mmol) of N-benzylpiperazine was added with ice cooling. The mixture was stirred at 0° C. for 0.5 hour, and at room temperature for 2.5 hours. Then, the reaction mixture was diluted with ethyl acetate, and the dilution was washed with water and a saturated aqueous solution of sodium chloride in this order. The washed system was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 2.61 g (34%) of the captioned compound.

Workup

waitat room temperature for 2.5 hours
washthe dilution was washed with water
dry with materialThe washed system was dried over sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-fb1d8cb063b44b8f9fd9c4bf85c538ca
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268128B2

Reaction notes

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