Acetic Anhydride → HCID 21428809, compound

HRID 437679Notes

Reaction equation

HRID 437679 reaction equation
[NH2:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([OH:15])[CH2:11][CH2:10]1)=[O:5].[C:28](OC(=O)C)(=[O:30])[CH3:29].[OH-].[NH4+]>O>[C:28]([NH:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([OH:15])[CH2:11][CH2:10]1)=[O:5])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 21428831HCID 21428831, compound

Product 1

HCID 21428809HCID 21428809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.8 parts of 2-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluorobenzamide, 5.5 parts of acetic acid anhydride and 55 parts of water is stirred and heated for 30 minutes in a water-bath at about 80° C. The reaction mixture is cooled and alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The aqueous phase is separated and extracted with trichloromethane. The combined organic phases are washed three times with water, dired, filtered and evaporated. The oily residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 4.5 parts of 2-(acetylamino)-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluorobenzamide; mp. 175.1° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe product is extracted with trichloromethane
  3. customThe aqueous phase is separated
  4. extractionextracted with trichloromethane
  5. washThe combined organic phases are washed three times with water
  6. filtrationdired, filtered
  7. customevaporated
  8. customThe oily residue is crystallized from 4-methyl-2-pentanone
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-2f2ac863501a463ba8360bf2a10d6a91
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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