Acetic Anhydride → HCID 21428970, compound

HRID 437676Notes

Reaction equation

HRID 437676 reaction equation
[NH2:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][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][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:24])[CH2:11][CH2:10]1)=[O:5].[C:30](OC(=O)C)(=[O:32])[CH3:31].[OH-].[NH4+]>O>[C:30]([NH:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH:12]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:24])[CH2:13][CH2:14]1)=[O:5])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 21428835HCID 21428835, compound

Product 1

HCID 21428970HCID 21428970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1 part of 2-amino-N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-4-fluorobenzamide, 1 part of acetic acid anhydride and 15 parts of water is stirred for 30 minutes in a water-bath at 80°-90° C. The reaction mixture is cooled and alkalized with an ammonium hydroxide solution. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 0.5 parts of 2-(acetylamino)-N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethyl}-4-fluorobenzamide; mp. 210° 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 crystallized from 4-methyl-2-pentanone
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-eb0cc4983fda4398a59a46905d8eebba
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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