Potassium Iodide → 1-[1-(4-fluorophenyl)ethyl]-N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine

HRID 1856568Notes

Reaction equation

HRID 1856568 reaction equation
Cl[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)[CH3:3].[C:11]1([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:26]3[NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[N:27]=3)[CH2:21][CH2:20]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH:2]([N:27]2[C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=[C:26]2[NH:25][CH:22]2[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:20][CH2:21]2)[CH3:3])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 49617391-(1-Chloroethyl)-4-fluorobenzeneHCID 12891523N-[1-(2-Phenylethyl)piperidin-4-yl]-1H-benzimidazol-2-amine

Product 1

HCID 128917201-[1-(4-fluorophenyl)ethyl]-N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amineYield 40.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1.6 parts of 1-(1-chloroethyl)-4-fluorobenzene, 3.2 parts of N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 1 part of sodium carbonate, 0.1 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, 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 2,2'-oxybispropane. The product is filtered off and dried, yielding 1.8 parts (40.7%) of 1-[1-(4-fluorophenyl)ethyl]-N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 161.7° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. additionpoured 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 2,2'-oxybispropane
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-a8e3d9e74afb4b0ab692089528e9444c
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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