Acetic Anhydride → HCID 86741817, compound

HRID 2309664Notes

Reaction equation

HRID 2309664 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH:33][CH3:34])[CH2:19][CH2:18]1.[C:36]([O:39][C:40](=[O:42])[CH3:41])(=[O:38])[CH3:37].[OH-:43].[NH4+]>O>[C:40]([OH:39])(=[O:42])[C:41]([OH:1])=[O:43].[C:36]([CH2:34][NH:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]([NH:25][CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][CH:17]([CH2:16][C:8]2[N:7]([CH2:6][C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH2:18][CH2:19]1)=[O:35])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 14518074HCID 14518074, compound

Product 1

HCID 86741817HCID 86741817, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 2.9 parts of N-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-ethyl]-2-(methylamino)benzamide, 10 parts of acetic acid anhydride and 20 parts of water was stirred and heated for 3 hours at 100° C. The reaction mixture was cooled, water was added and the whole was made alkaline with ammonium hydroxide. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified twice by column chromatography over silica gel using each time a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the ethanedioate salt in ethanol, yielding 0.2 parts (4.3%) of 2-(acetylmethylamino)-N-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]-methyl]-1-piperidinyl]ethyl]benzamide ethanedioate (2:5); mp. 146.8° C. (511).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified twice by column chromatography over silica gel using each time
  7. additiona mixture of trichloromethane and methanol
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0bee2a8969f94cadb2638c90e31b32cc
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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