Lawesson's reagent → Benzyl 4-carbamothioylpiperidine-1-carboxylate

HRID 1497646Notes

Reaction equation

HRID 1497646 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=O)[NH2:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[S:29])[NH2:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2776131benzyl 4-(aminocarbonyl)tetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 18969329Benzyl 4-carbamothioylpiperidine-1-carboxylateYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl-4-carbamoylpiperidine-1-carboxylate (7.5 g, 38.6 mmol) was dissolved in THF (160 mL) and Lawesson's reagent (6.9 g, 17.1 mmol) was added. After 4 h the solvent was evaporated and the residue purified by flash-chromatography on silica gel (DCM-MeOH 95/5) affording 1.8 g (23%) of the title compound, crystallized from MeOH.

Workup

  1. customAfter 4 h the solvent was evaporated
  2. customthe residue purified by flash-chromatography on silica gel (DCM-MeOH 95/5)

Sources & evidence

ORD record
ord-619ea21751164cf6baca178aa6e0a9f0
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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