Lawesson's reagent → HCID 86704187, compound

HRID 1497650Notes

Reaction equation

HRID 1497650 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:10]([NH2:12])=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1COCC1>[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:10](=[S:22])[NH2:12])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57481588HCID 57481588, compound

Product 1

HCID 86704187HCID 86704187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-cyclopropylpiperidine-4-carboxamide was suspended in dry THF (20 mL) and Lawesson's reagent (2.7 g, 6.67 mmol) was added. After refluxing for 6 h the solvent was concentrated under reduced pressure. The residue was dissolved in a ethyl acetate/MeOH mixture and washed with saturated aqueous NaHCO3. The aqueous phase was back-extracted with ethyl acetate and evaporated to dryness. The crude product was treated with ethanol and filtered. The white solid was dried under high vacuum affording 2.7 g of the title compound.

Workup

  1. temperatureAfter refluxing for 6 h the solvent
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a ethyl acetate/MeOH mixture
  4. washwashed with saturated aqueous NaHCO3
  5. extractionThe aqueous phase was back-extracted with ethyl acetate
  6. customevaporated to dryness
  7. additionThe crude product was treated with ethanol
  8. filtrationfiltered
  9. customThe white solid was dried under high vacuum

Sources & evidence

ORD record
ord-1ad0c3b55a8740e0ba07ba534e5b775a
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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