Water → HCID 131718513, compound

HRID 1109733Notes

Reaction equation

HRID 1109733 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[NH:22][C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[N:19]=3)[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:34][CH2:35][O:36][CH2:37][CH3:38].O>C(#N)C>[CH3:4][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:14][CH:15]([C:18]3[N:22]([CH2:34][CH2:35][O:36][CH2:37][CH3:38])[C:21]4[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=4[N:19]=3)[CH2:16][CH2:17][N:12]2[CH3:13])=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 10383076HCID 10383076, compound

Product 1

HCID 131718513HCID 131718513, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3.47 g of 2-[1-((4-(1,1-dimethylethyl)phenyl) methyl)piperidine-4-yl]-1H-benzimidazole in 80 ml of acetonitrile, 1.38 g of potassium carbonate and 1.08 ml of 2-chloroethyl-ethyl ether are added and the mixture is refluxed for 8 hours; then is left to cool and poured onto 200 ml of water; it is extracted with ether (3×30 ml) and the ethereal layer is washed with water (3×20 ml) and dried over anhydrous sodium sulfate. The oil obtained by elimination of the ether is purified by column chromatography by using chloroform/methanol (98/2) as eluent, thus obtaining 2 g of 2-[1-((4-(1.1-dimethylethyl)phenyl(methyl) piperidine-4-yl]-1-(2-ethoxyethyl)-1H-benzimidazole. Mp: 51°-53° C.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. waitthen is left
  3. temperatureto cool
  4. extractionit is extracted with ether (3×30 ml)
  5. washthe ethereal layer is washed with water (3×20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe oil obtained by elimination of the ether
  8. customis purified by column chromatography

Sources & evidence

ORD record
ord-71e2aa6410c14260b285695367ac45b7
Source dataset
uspto-grants-1994_06
Patent number
US05322850

Reaction notes

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