Benzene → N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide

HRID 437667Notes

Reaction equation

HRID 437667 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])=[CH:4][CH:3]=1.Cl.[O:14]=[C:15]1[N:19]([CH2:20][CH2:21][C:22]#[N:23])[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]1[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.C1C=CC=CC=1>CO>[C:22]([CH2:21][CH2:20][N:19]1[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=3)[CH2:30][CH2:29]2)[C:15]1=[O:14])#[N:23]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 848531-(4-Fluorobenzoyl)aziridineHCID 214289232,3-dihydro-2-oxo-3-(4-piperidinyl)-1H-benzimidazole-1-propanenitrile hydrochloride

Product 1

HCID 21428991N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.68 parts of 1-(4-fluorobenzoyl)aziridine, 3.07 parts of 2,3-dihydro-2-oxo-3-(4-piperidinyl)-1H-benzimidazole-1-propanenitrile hydrochloride, 1.65 parts of N,N-diethylethanamine, 10.8 parts of benzene and 1.6 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and poured onto water. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2-propanol. The product is filtered off and recrystallized from 2-propanol, yielding 1part of N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide; mp. 172.2° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2-propanol
  9. filtrationThe product is filtered off
  10. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-d430f8b65d8c48dfbff9d02feace18b1
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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