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Sodium Carbonate → 1-{3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl}-1,3-dihydro-5-methyl-2H-benzimidazol-2-one

HRID 258857
Notes
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Reaction equation

HRID 258857 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=2[NH:11][C:10]1=[O:19])(=O)=O.Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:29])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([CH:30]2[CH2:35][CH2:34][N:33]([CH2:6][CH2:7][CH2:8][N:9]3[C:13]4[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=4[NH:11][C:10]3=[O:19])[CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochlorideHCID 214248263-(2,3-dihydro-5-methyl-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonate

Product 1

HCID 214248241-{3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl}-1,3-dihydro-5-methyl-2H-benzimidazol-2-oneYield 6.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 5.68 parts of 3-(2,3-dihydro-5-methyl-2-oxo-1H-benzimidazol-1-yl)propyl methanesulfonate, 4.8 parts of (4-fluorophenyl) (4-piperidinyl) methanone hydrochloride, 3.7 parts of sodium carbonate and 45 parts of N,N-dimethylformamide is stirred for 1 hour at 50°-60° C. The reaction mixture is cooled to room temperature and poured onto water. 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 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and recrystallized twice from 4-methyl-2-pentanone, yielding 0.5 parts (6.5%) of 1-{3-[4-(4-fluorobenzoyl)-1-piperidinyl]propyl}-1,3-dihydro-5-methyl-2H-benzimidazol-2-one; mp. 149° C.

Workup

  1. additionpoured onto water
  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 10% of methanol as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe residue is crystallized from 4-methyl-2-pentanone
  11. filtrationThe product is filtered off
  12. customrecrystallized twice from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-4daabaafd0934d1696374426da32ca7b
Source dataset
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04035369

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes