Acetic Anhydride → HCID 20343984, compound

HRID 2049883Notes

Reaction equation

HRID 2049883 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(C1(C2C=CC=CC=2SC2C=CC(F)=CC=2)CCNCC1)#N.[C:46](OC(=O)C)(=[O:48])[CH3:47]>N1C=CC=CC=1>[C:46]([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:48])[CH3:47]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 20343972HCID 20343972, compoundHCID 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, free amino acid of Example 30, 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 and 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, once with 15 ml of saturated sodium chloride solution and dried. The resulting product is recrystallized from acetone-ether to provide 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. additiontreated 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, once with 15 ml of saturated sodium chloride solution
  6. customdried
  7. customThe resulting product is recrystallized from acetone-ether

Sources & evidence

ORD record
ord-7c77c387c066427b8cfe5557ff4a35f5
Source dataset
uspto-grants-1980_04
Patent number
US04198419

Reaction notes

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