1,5-Dibromopentane → HCID 19876776, compound

HRID 1886020Notes

Reaction equation

HRID 1886020 reaction equation
[C:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:17][CH2:18][CH2:19][OH:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.[OH-].[Na+]>ClCCl.O>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:20][CH2:19][CH2:18][CH2:17][C:9]1[N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 28724753-(1-benzyl-1H-benzimidazol-2-yl)propan-1-ol

Product 1

HCID 19876776HCID 19876776, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(phenylmethyl)-2-benzimidazolepropanol (3.0 g), 1,5-dibromopentane (7.77 g), TAB (0.5 g) and 40% sodium hydroxide (5 ml) in dichloromethane (10 ml) was stirred at room temperature for 6 h under nitrogen. The mixture was diluted with water (100 ml) and extracted with dichloromethane (2×100 ml). The dried extracts were evaporated in vacuo to give an oil. Purification by FCC eluting with hexane-ether (10:0→0:10) gave the title compound as a colourless oil (0.98 g).

Workup

  1. extractionextracted with dichloromethane (2×100 ml)
  2. customThe dried extracts were evaporated in vacuo
  3. customto give an oil
  4. customPurification by FCC
  5. washeluting with hexane-ether (10:0→0:10)

Sources & evidence

ORD record
ord-236c461afdd14089ba46aae411276ca2
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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