Methyl Isobutyl Ketone → N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amine

HRID 1856569Notes

Reaction equation

HRID 1856569 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]3[NH:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[N:17]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(O[CH2:36][CH2:37][C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16]3[N:17]([CH2:36][CH2:37][C:38]4[S:39][CH:40]=[CH:41][CH:42]=4)[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 36820342-Thiopheneethanol tosylateHCID 12891523N-[1-(2-Phenylethyl)piperidin-4-yl]-1H-benzimidazol-2-amine

Product 1

HCID 12891721N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amineYield 23.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.2 parts of N-[1-(2-phenylethyl)-4-piperidinyl]-1H-benzimidazol-2-amine, 2.9 parts of [2-(2-thienyl)ethyl] 4-methylbenzenesulfonate, 1 part of sodium carbonate and 135 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with 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 2,2'-oxybispropane and 2-propanone, yielding 1 part (23.2%) of N-[1-(2-phenylethyl)-4-piperidinyl]-1-[2-(2-thienyl)ethyl]-1H-benzimidazol-2-amine; mp. 118.3° C.

Workup

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

Sources & evidence

ORD record
ord-85e86dae2d544bd2901faccba6cb8981
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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