Lawesson's reagent → 1-(3,5-Dichloropyridin-4-yl)piperidine-4-carbothioamide

HRID 1622334Notes

Reaction equation

HRID 1622334 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=O)[CH2:10][CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1.C(=O)([O-])O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:27])[NH2:16])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

Product 1

HCID 583782791-(3,5-Dichloropyridin-4-yl)piperidine-4-carbothioamideYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (40 mg, 0.15 mmol) in THF (2 mL) was added Lawesson's reagent (71 mg, 0.18 mmol) and the mixture was heated at reflux for 2.5 h. After cooling to r.t. the mixture was poured into a saturated solution of sodium hydrogen carbonate (20 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 99:1) to furnish the title compound as a white solid (21 mg, 40%), m/z (ESI) C11H14Cl2N2S requires 290.0280 found [M+H]+ 290.0280.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2.5 h
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic extracts were washed with water (20 mL), brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 99:1)

Sources & evidence

ORD record
ord-9e630f9adb764fdf83f891e3dbcde354
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…