Chloride → HCID 20343975, compound

HRID 2049876Notes

Reaction equation

HRID 2049876 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:10](Cl)=[O:11])[CH2:6][CH2:5]1)(=O)C.[Cl-].[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>C(O)C.O.CCOCC>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[CH2:28]([O:29][C:10]([C:7]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]1)=[O:11])[CH3:27]

Participants

7

Reactant 3

HCID 312ChlorideHCID 971Oxalic AcidHCID 20343950HCID 20343950, compound

Product 1

HCID 20343975HCID 20343975, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2 g of 1-acetyl-4-(2-phenylthiophenyl)-piperidine-4-carbonyl chloride, Example 16, in 50 ml of absolute ethyl alcohol saturated with anhydrous chloride is stirred at reflux for 64 hours. Thereafter, the excess acid and alcohol is removed under reduced pressure, leaving a clear, glassy residue. The residue is dissolved in 30 ml of water and the aqueous solution is extracted with ethyl acetate. The aqueous solution is basified with potassium carbonate, liberating an oil. The oil is dissolved in ether and the ethereal solution is dried before concentrating to dryness, leaving a brownish oil. The oil, in ether, is converted to its oxalic acid salt which is recrystallized from a methyl alcohol-acetone-ether mixture to provide 4-ethoxycarbonyl-4-(2-phenylthiophenyl)-piperidine oxalate.

Workup

  1. temperatureat reflux for 64 hours
  2. customThereafter, the excess acid and alcohol is removed under reduced pressure
  3. customleaving a clear, glassy residue
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. dissolutionThe oil is dissolved in ether
  6. customthe ethereal solution is dried
  7. concentrationbefore concentrating to dryness
  8. customleaving a brownish oil
  9. customis recrystallized from a methyl alcohol-acetone-ether mixture

Sources & evidence

ORD record
ord-6903fca8ecca494ebd90730f95741063
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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