Potassium Iodide → HCID 12891749, compound

HRID 1856579Notes

Reaction equation

HRID 1856579 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]=3[N:26]=2)[CH2:20][CH2:19]1.Cl[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:49][C:46]1[CH:47]=[CH:48][C:43]([CH2:42][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[N:18]2[CH2:19][CH2:20][CH:21]([NH:24][C:25]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:28]4[CH:37]=[CH:38][CH:39]=[CH:40][C:27]=4[N:26]=3)[CH2:22][CH2:23]2)=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 96024-Fluorobenzyl chlorideHCID 10340Sodium CarbonateHCID 86737172HCID 86737172, compound

Product 1

HCID 12891749HCID 12891749, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 5.5 parts of N-[1-(1H-benzimidazol-2-yl)-4-piperidinyl]-1-(phenylmethyl)-1H-benzimidazol-2-amine dinitrate, 1.5 parts of 1-(chloromethyl)-4-fluorobenzene, 5 parts of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight using a water-separator. The reaction mixture is poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane. The product is filtered off and dried, yielding 1.5 parts (28.3%) of N-{1-[1-(4-fluorophenylmethyl)-1H-benzimidazol-2-yl]-4-piperidinyl}-1-(phenylmethyl)-1H-benzimidazol-2-amine; mp. 163.9° C.

Workup

  1. temperaturerefluxed overnight
  2. additionThe reaction mixture is poured onto water
  3. customthe layers are separated
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe residue is crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-0ea7b298e0b34b208729f4c3a6009c46
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

Loading…