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

HRID 20240Notes

Reaction equation

HRID 20240 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-8f7399466a564aa9b6b09e7f893da309
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

Loading…