Lawesson's reagent → Ethyl 3-(3,4-difluorophenyl)-2-thioxopiperidine-3-carboxylate

HRID 71111Notes

Reaction equation

COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:25]=[C:26]([C:31]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][NH:33][C:32]2=O)[CH:27]=[CH:28][C:29]=1[F:30]>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:25]=[C:26]([C:31]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][NH:33][C:32]2=[S:10])[CH:27]=[CH:28][C:29]=1[F:30]

Participants

Conditions

Temperature: 110 °C

Procedure

Under an argon atmosphere, Lawesson's reagent (1.00 g) was added to a suspension of ethyl 3-(3,4-difluorophenyl)-2-oxopiperidine-3-carboxylate (1.00 g) in toluene (20 mL) at room temperature. The reaction mixture was stirred at 110° C. for 4 hr, and allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (859 mg).

Workup

temperatureto cool to room temperature
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-3c8ee0485f7d48f3af8d7a9297adf0a4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

Loading…