Lawesson's reagent → HCID 14294064, compound

HRID 1381703Notes

Reaction equation

HRID 1381703 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=O)[CH:6]=[CH:7][CH:8]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1C=CC=CC=1>[S:29]=[C:10]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 14294054HCID 14294054, compound

Product 1

HCID 14294064HCID 14294064, compoundYield 182.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 135.6 g of 1-[[3-(trifluoromethyl)phenyl]acetyl]piperidine, 101.1 g of Lawesson's reagent and 400 ml of benzene was heated at reflux for 6 hours, cooled and concentrated in vacuo. The residue was taken up in dichloromethane, filtered through a bed of neutral alumina with 3 liters of dichloromethane elution. The filtrate was concentrated in vacuo. The resulting oil was vacuum distilled giving 131 g of 1-[1-thioxo-2-[3-(trifluoromethyl)phenyl]ethyl]piperidine, bp 181°-182° C. (3.0 mmHg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered through a bed of neutral alumina with 3 liters of dichloromethane elution
  6. concentrationThe filtrate was concentrated in vacuo
  7. distillationdistilled

Sources & evidence

ORD record
ord-ad82ff5fb68842359f2fe9bb7a1bc9c8
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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