4-[3-(Trifluoromethyl)phenyl]-4-piperidinol → 4-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

HRID 1670774Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])O.[Na+]>FC(CC(O)=O)(F)F>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-[3-(Trifluoromethyl)phenyl]-4-hydroxypiperidine (Aldrich Co., 2.2 g) was suspended in trifluoromethylacetic acid (10 ml) and the mixture was stirred with heating at 80° C. for 5 hr. After completion of the reaction, the reaction mixture was cooled to room temperature, neutralized with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine (791 mg, yield 67%).

Workup

customAfter completion of the reaction
temperaturethe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
customThe organic layer was dried
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-6170490577394ebbabc468b5e3263f53
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994196B2

Reaction notes

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