Methyl Isobutyl Ketone → 1-{3-[4-(diphenylmethoxy)-1-piperidinyl]propyl}-1H-benzimidazole

HRID 355000Notes

Reaction equation

HRID 355000 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[CH:6]1.Cl.[C:15]1([CH:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:29]1([CH:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][N:5]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[N:7]=[CH:6]3)[CH2:25][CH2:24]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 131055171-(3-Chloropropyl)-1H-benzimidazoleHCID 441535184-(Diphenylmethoxy)piperidinium chloride

Product 1

HCID 131056161-{3-[4-(diphenylmethoxy)-1-piperidinyl]propyl}-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 6 parts of 1-(3-chloropropyl)-1H-benzimidazole, 7.6 parts of 4-(diphenylmethoxy)piperidine hydrochloride, 10.6 parts of sodium carbonate and 200 parts of 4-methyl-2-pentanone is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, water is added and the layers are separated. The 4-methyl-2-pentanone-phase is dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 1-{3-[4-(diphenylmethoxy)-1-piperidinyl]propyl}-1H-benzimidazole; mp. 110.2° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers are separated
  3. dry with materialThe 4-methyl-2-pentanone-phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe oily residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. customThe oily residue is crystallized from 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customdried

Sources & evidence

ORD record
ord-f7d905fbbb004741b264b8e778ccb250
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Reaction notes

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