Water → HCID 14852375, compound

HRID 1756140Notes

Reaction equation

HRID 1756140 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH:15]([C:24]2[N:25]=[CH:26][NH:27][CH:28]=2)[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:27]1[CH:28]=[C:24]([CH:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:25]=[CH:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178420252HCID 178420252, compound

Product 1

HCID 14852375HCID 14852375, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

2,0 g of benzylbromide in 5 ml of toluene is added dropwise to the mixture of 4-(1,3-diphenylpropyl)-1H-imidazole (2,6 g), 48% NaOH (10 ml), toluene (20 ml) and tetrabutylammoniumbromide (0,2 g) at room temperature. After addition the reaction mixture is stirred at room temperature for 3 hours. Water is added and the toluene layer is separated. The toluene phase is then washed with water and evaporated to dryness. The residue contains the isomers 1-benzyl-4-(1,3-diphenylpropyl)-1H-imidazole and 1-benzyl-5-(1,3-diphenylpropyl)-1H-imidazole and the former is separated and purified by flash chromatography (methylene chloride-methanol 9,5:0,5).

Workup

  1. additionAfter addition the reaction mixture
  2. customthe toluene layer is separated
  3. washThe toluene phase is then washed with water
  4. customevaporated to dryness
  5. customthe former is separated
  6. custompurified by flash chromatography (methylene chloride-methanol 9,5:0,5)

Sources & evidence

ORD record
ord-677153133be24e7b962f4e5ce52817c9
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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