Lawesson's reagent → tert-Butyl 2-thioxo-1,4'-bipiperidin-1'-carboxylate

HRID 2366552Notes

Reaction equation

HRID 2366552 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C=CC=CC=1>[S:30]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66524582Tert-butyl 2-oxo-1,4'-bipiperidine-1'-carboxylate

Product 1

HCID 86082829tert-Butyl 2-thioxo-1,4'-bipiperidin-1'-carboxylateYield 128.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 2-oxo-1,4′-bipiperidin-1′-carboxylate (2.8 g) and Lawesson's reagent (2.0 g) in toluene (30 mL) was refluxed for one hour. Toluene was distilled off under reduced pressure, and the residue was diluted with dichloromethane, and washed with an aqueous 1N sodium hydroxide solution and saturated saline solution. This dichloromethane solution was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/2) to obtain the title compound (1.9 g, 64%) as a white powder.

Workup

  1. distillationToluene was distilled off under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washwashed with an aqueous 1N sodium hydroxide solution and saturated saline solution
  4. dry with materialThis dichloromethane solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/2)

Sources & evidence

ORD record
ord-ff1f1615cd8d44d88f9328bf4a1ecd50
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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