Methanol → N{2-[4-(2,3-dihydro-2-oxo-lH-benzimidazol-1-yl)-1-piperidinyl] ethyl}-4-fluoro-2-methoxybenzamide

HRID 437630Notes

Reaction equation

HRID 437630 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[C:4]([O:13][CH3:14])[CH:3]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[NH:23][C:22]2=[O:30])[CH2:17][CH2:16]1.CO>C1C=CC=CC=1>[O:30]=[C:22]1[N:21]([CH:18]2[CH2:17][CH2:16][N:15]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=3[O:13][CH3:14])[CH2:20][CH2:19]2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23]1

Participants

5

Reactant 3

HCID 887MethanolHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 214288101-(4-Fluoro-2-methoxybenzoyl)-aziridine

Product 1

HCID 54412965N{2-[4-(2,3-dihydro-2-oxo-lH-benzimidazol-1-yl)-1-piperidinyl] ethyl}-4-fluoro-2-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 8 parts of 1-(4-fluor-2-methoxybenzoyl)-aziridine, 3.8 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 54 parts of benzene and 8 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and 90 parts of benzene are added. The whole is washed with water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2-propanone. The product is filtered off and dried, yielding 4 parts of N{2-[4-(2,3-dihydro-2-oxo-lH-benzimidazol-1-yl)-1-piperidinyl] ethyl}-4-fluoro-2-methoxybenzamide; mp. 197.3° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. washThe whole is washed with water
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2-propanone
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-7054c6aab4284010a0a2eef3f8f6e6b3
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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