Lawesson's reagent → tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

HRID 1497644Notes

Reaction equation

HRID 1497644 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCOC.CC1OC(C=CC2C=C3CCCN4CCCC(=C34)C=2)=CC(=C(C#N)C#N)C=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:59])=CC=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[S:59])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 87949Lawesson's reagentHCID 27356461-(tert-Butoxycarbonyl)piperidine-4-carboxamideHCID 131734219Dme dcm 2

Product 1

HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateYield 186.7%

Procedure

To a solution of tert-butyl-4-carbamoylpiperidine-1-carboxylate (2.65 g, 11.62 mmol) in a DME/DCM 2:1 mixture (78 mL), Lawesson reagent (2.35 g, 5.81 mmol, 0.5 eq) was added and the mixture was stirred at r.t. overnight. The solvent was removed and the residue was taken up with ethyl acetate and washed with saturated aqueous K2CO3. The organic layer was separated, dried over Na2SO4 and concentrated to dryness. The residue was triturated with diethyl ether and dried to give 2.65 g (92%) of the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. washwashed with saturated aqueous K2CO3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-7d1e98ba6f04467fb6374ff3c4a35cc8
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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