Acetic Anhydride → HCID 20343955, compound

HRID 2049675Notes

Reaction equation

HRID 2049675 reaction equation
Br.[C:2]1([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([N:18]1[CH2:17][CH2:16][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:21]([OH:23])=[O:22])[CH2:20][CH2:19]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70584085HCID 70584085, compound

Product 1

HCID 20343955HCID 20343955, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 8 g of 4-(2-phenylthiophenyl)piperidine-4-carboxylic acid hydrobromide and 10 ml of acetic anhydride in 50 ml of pyridine is refluxed for 4 hours. Thereafter, any excess pyridine is removed by distillation under vacuum and the residue is triturated in 100 ml of 1 N hydrochloric acid before being extracted thrice with chloroform. The combined chloroform extracts are successively washed well with water, dried and concentrated under vacuum. The residue is recrystallized from boiling acetone to provide 1-acetyl-4-(2-phenylthiophenyl)piperidine-4-carboxylic acid.

Workup

  1. temperatureis refluxed for 4 hours
  2. customThereafter, any excess pyridine is removed by distillation under vacuum
  3. customthe residue is triturated in 100 ml of 1 N hydrochloric acid
  4. extractionbefore being extracted thrice with chloroform
  5. washThe combined chloroform extracts are successively washed well with water
  6. customdried
  7. concentrationconcentrated under vacuum
  8. customThe residue is recrystallized

Sources & evidence

ORD record
ord-731b8cc3e5c44678ac18b619ba5725db
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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