Phosphorus sulfide (P2S5) → HCID 19858456, compound

HRID 1381704Notes

Reaction equation

HRID 1381704 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=O)=[O:5])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16]>C1(C)C=CC=CC=1>[S:16]=[C:11]1[CH2:12][CH2:13][CH2:14][N:9]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 12249490HCID 12249490, compound

Product 1

HCID 19858456HCID 19858456, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-[(ethoxycarbonyl)acetyl]piperidine, 131 g of phosphorus pentasulfide and one liter of toluene was stirred for 96 hours. The solvent was decanted and saved. The gum was washed with 250 ml of toluene. The toluene solutions were combined and concentrated in vacuo. The residue was dissolved in dichloromethane and percolated through a bed of hydrous magnesium silicate, washing with the same solvent. The filtrate and wash were combined and concentrated in vacuo, giving 92 g of ethyl 3-thioxo-N-piperidinepropionate.

Workup

  1. customThe solvent was decanted
  2. washThe gum was washed with 250 ml of toluene
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashing with the same solvent
  6. washThe filtrate and wash
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2868738ef99476e8efc1f1de7ffa1f5
Source dataset
uspto-grants-1989_02
Patent number
US04803280

Reaction notes

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