Phosphorus sulfide (P2S5) → HCID 19858456, compound

HRID 2073362Notes

Reaction equation

HRID 2073362 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-b9f75d304af44349b6d79b0bb94fb7c6
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

Loading…