Toluene → 1-acetyl-3-[2-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]ethyl]-1,3-dihydro-2H-benzimidazol-2-one

HRID 126875Notes

Reaction equation

HRID 126875 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:35])[CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[NH:27][C:26]3=[O:34])[CH2:19][CH2:18]2)=[CH:11][CH:10]=1.CC1C=CC=CC=1.[OH-].[NH4+]>O>[C:1]([N:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:25]([CH2:24][CH2:23][N:20]2[CH2:19][CH2:18][CH:17]([CH2:16][C:15]([C:12]3[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=3)=[O:35])[CH2:22][CH2:21]2)[C:26]1=[O:34])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 20288037HCID 20288037, compound

Product 1

HCID 202880511-acetyl-3-[2-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]ethyl]-1,3-dihydro-2H-benzimidazol-2-oneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.1 parts of acetic acid anhydride, 5 parts of 1-[2-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]ethyl]-1,3-dihydro-2H-benzimidazol-2-one and 56 parts of methylbenzene is stirred and refluxed for 4 hours. The reaction mixture is cooled and water and ammonium hydroxide are added. Upon stirring, the product is crystallized. It is filtered off, washed with water and dried in vacuo, yielding 2.2 parts (40%) of 1-acetyl-3-[2-[4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperidinyl]ethyl]-1,3-dihydro-2H-benzimidazol-2-one; mp. 149.2° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. stirringUpon stirring
  4. customthe product is crystallized
  5. filtrationIt is filtered off
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d372e32243dd499d964958a42965534f
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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