Lawesson's reagent → HCID 78207191, compound

HRID 2047637Notes

Reaction equation

HRID 2047637 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.O=[C:24]1[CH2:29][CH:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:26][NH:25]1>C1(C)C=CC=CC=1>[NH:25]1[CH2:26][CH2:27][CH:28]([C:30]([O:32][CH3:33])=[O:31])[CH2:29][C:24]1=[S:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 23093678Methyl 2-oxopiperidine-4-carboxylate

Product 1

HCID 78207191HCID 78207191, compoundYield 176.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add Lawesson's reagent (9.2 g, 22.7 mmol) to a solution of methyl 2-oxopiperidine-4-carboxylate (6.5 g, 41.4 mmol) in toluene (83 mL) and heat to reflux for 2 hours. Cool the solution and concentrate to dryness under reduced pressure. Purify the residue by flash chromatography on silica gel, eluting with ethyl acetate:dichloromethane (gradient 5-15%) to afford the title compound (6.95 g). 1H NMR (CDCl3) δ 1.97 (m, 1H), 2.17 (m, 1H), 2.78 (m, 1H), 3.03 (m, 1H), 3.24 (m, 1H), 3.39 (m, 1H), 3.49 (m, 1H), 3.72 (s, 3H), 8.48 (bs, 1H).

Workup

  1. temperatureheat
  2. temperatureto reflux for 2 hours
  3. temperatureCool the solution
  4. concentrationconcentrate to dryness under reduced pressure
  5. customPurify the residue by flash chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c6e8977ab0c64951861756e0e8f3bf6d
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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