Dimethylformamide → 4-fluoro-N-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]benzamide

HRID 1856562Notes

Reaction equation

HRID 1856562 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[N:23]=[C:22]2[NH:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:16][CH:15]=1.CN(C)C=O>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:10][CH2:9][N:34]2[CH2:35][CH2:36][CH:31]([NH:30][C:22]3[N:21]([CH2:20][C:17]4[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[N:23]=3)[CH2:32][CH2:33]2)=[O:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 848531-(4-Fluorobenzoyl)aziridineHCID 123618Tecastemizole

Product 1

HCID 128916844-fluoro-N-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]benzamideYield 19%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 3.96 parts of 1-(4-fluorobenzoyl)aziridine, dissolved in 16 parts of benzene, are added 3.25 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 90 parts of benzene and 45 parts of N,N-dimethylformamide. The whole is stirred and refluxed for 5 hours. The reaction mixture is cooled and poured onto water. The layers are separated and the aqueous phase is extracted with methylbenzene. The combined organic phases are dried, filtered and evaporated. The residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane, yielding 1part (19%) of 4-fluoro-N-[2-{4-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-ylamino]-1-piperidinyl}ethyl]benzamide; mp. 193.7° C.

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with methylbenzene
  6. customThe combined organic phases are dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from a mixture of 2-propanone and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-9c9e1d83788e4ae1b3606c7964be1d8b
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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