Acetic Anhydride → HCID 20343984, compound

HRID 2049691Notes

Reaction equation

HRID 2049691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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: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:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([C:21]([OH:23])=[O:22])[CH2:20][CH2:19]1)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20343982HCID 20343982, compound

Product 1

HCID 20343984HCID 20343984, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.7 g of 4-[2-(4-fluorophenylthio)phenyl]piperidine-4-carboxylic acid and 0.83 ml of acetic anhydride in 4.2 ml of pyridine is stirred at reflux for 4 hours. Thereafter, the excess pyridine is removed by rotary evaporation and the residue is taken up in 10 ml of water, where it is treated with 10 ml of 1 N hydrochloric acid. The acidic mixture is extracted thrice with 20 ml portions of an ether-benzene (1:1) mixture and the combined extracts are successively washed twice with 40 ml portions of water, washed once with a 15 ml portion of a saturated sodium chloride solution and dried. The resulting residue is recrystallized from an acetone-ether (1:4) mixture providing 1-acetyl-4-[2-(4-fluorophenylthio)phenyl]piperidine-4-carboxylic acid.

Workup

  1. temperatureat reflux for 4 hours
  2. customThereafter, the excess pyridine is removed by rotary evaporation
  3. additionwhere it is treated with 10 ml of 1 N hydrochloric acid
  4. extractionThe acidic mixture is extracted thrice with 20 ml portions of an ether-benzene (1:1) mixture
  5. washthe combined extracts are successively washed twice with 40 ml portions of water
  6. washwashed once with a 15 ml portion of a saturated sodium chloride solution
  7. customdried
  8. customThe resulting residue is recrystallized from an acetone-ether (1:4) mixture

Sources & evidence

ORD record
ord-abe5e65692734db3b891bfbcfef45689
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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