5-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → HCID 21428799, compound

HRID 437633Notes

Reaction equation

HRID 437633 reaction equation
[Br:1][CH2:2][CH2:3][NH:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:22](=[O:24])[NH:23][C:19]=2[CH:18]=1>CN(C)C=O>[BrH:1].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]2[N:21]([CH:25]3[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][NH:4][C:5](=[O:15])[C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[N+:12]([O-:14])=[O:13])[CH2:29][CH2:30]3)[C:22](=[O:24])[NH:23][C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 3017373N-(2-Bromoethyl)-2-nitrobenzene-1-carboximidic acid

Product 1

HCID 21428799HCID 21428799, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 parts of N-(2-bromoethyl)-2-nitrobenzamide, 1.55 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one and 27 parts of N,N-dimethylformamide is stirred and refluxed for 5 hours. The reaction mixture is evaporated and the oily residue is crystallized from ethanol. The product is filtered off and dried, yielding 2.2 parts (67%) of N-{2-[4-(5-chloro-2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-nitrobenzamide hydrobromide. hemihydrate; mp. 273.2° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe reaction mixture is evaporated
  3. customthe oily residue is crystallized from ethanol
  4. filtrationThe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-c3f6cfc090ed4d929007242e546b3cfe
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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