Acetic Anhydride → HCID 21428813, compound

HRID 437678Notes

Reaction equation

HRID 437678 reaction equation
[NH2:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=3[NH:17][C:16]2=[O:25])[CH2:11][CH2:10]1)=[O:5].[C:31](OC(=O)C)(=[O:33])[CH3:32].[OH-].[NH4+]>O>[C:31]([NH:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=3[NH:17][C:16]2=[O:25])[CH2:11][CH2:10]1)=[O:5])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 21428847HCID 21428847, compound

Product 1

HCID 21428813HCID 21428813, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.8 parts of 2-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1yl)-1-piperidinyl]ethyl}-4-fluorobenzamide, 1 part of acetic acid anhydride and 10 parts of water is stirred for 30 minutes in a water-bath at 80°-90° C. The reaction mixture is cooled, alkalized with ammonium hydroxide and the product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 0.5 parts of 2-(acetylamino)-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-4-fluorobenzamide; mp. 196.5° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionthe product is extracted with trichloromethane
  3. customThe extract is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-a3a5f82862ed4e38ac43b1bb97a7e772
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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