Acetic Anhydride → HCID 20343955, compound

HRID 2049874Notes

Reaction equation

HRID 2049874 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, Example 14, and 10 ml of acetic anhydride in 50 ml of pyridine is refluxed for 4 hours. Thereafter, the pyridine is removed by distillation in vacuo and the residue is triturated with 100 ml of 1 N hydrochloric acid. The residue is extracted thrice with portions of chloroform and the combined chloroform extracts are successively washed twice with water, dried, and concentrated. The residue is recrystallized from acetone to provide 1-acetyl-4-(2-phenylthiophenyl)piperidine-4-carboxylic acid.

Workup

  1. temperatureis refluxed for 4 hours
  2. customThereafter, the pyridine is removed by distillation in vacuo
  3. customthe residue is triturated with 100 ml of 1 N hydrochloric acid
  4. extractionThe residue is extracted thrice with portions of chloroform
  5. washthe combined chloroform extracts are successively washed twice with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-2b45a360e7da45edb987d9a6890b55d1
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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