Ethyl Thioglycolate → HCID 12414524, compound

HRID 2163666Notes

Reaction equation

HRID 2163666 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(O)C>[C:1]([N:9]1[CH2:14][CH2:13][C:12]([S:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12185Ethyl ThioglycolateHCID 12414561Methyl 1-benzoyl-4-oxo-3-piperidinecarboxylate

Product 1

HCID 12414524HCID 12414524, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-benzoyl-3-methoxycarbonyl-4-piperidone (12 g; 0.046 mole) in absolute ethanol (150 cc), cooled to -10° C, is saturated with dry hydrochloric gas. Ethyl mercapto-acetate (10.8 g; 0.092 mole) is added thereto and a slight stream of hydrochloric gas is further passed therethrough at -10° C during 5 hours. After leaving the reaction mixture aside at room temperature during 70 hours, it is evaporated to dryness and the residue is dissolved in ether. The organic phase is washed with a 5% sodium bicarbonate solution and with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting 1-benzoyl-4-ethoxycarbonylmethylthio-3-methoxycarbonyl-1,2,5,6-tetrahydro-pyridine is obtained as an oil (Yield: 100%) and used directly in the next step:

Workup

  1. customwith dry hydrochloric gas
  2. customAfter leaving the reaction mixture aside at room temperature during 70 hours
  3. customit is evaporated to dryness
  4. dissolutionthe residue is dissolved in ether
  5. washThe organic phase is washed with a 5% sodium bicarbonate solution and with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e7c6b2fc3f44e4988795b4c08070923
Source dataset
uspto-grants-1979_01
Patent number
US04136186

Reaction notes

Loading…