Benzene → 1-Benzylindole

HRID 1638764Notes

Reaction equation

HRID 1638764 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].C1C=CC=CC=1>O>[CH2:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 798IndoleHCID 7503Benzyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 969131-BenzylindoleYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Indole (1.17 g, 0.01 mol) was added to a mixture of benzyl chloride (1.90 g, 0.015 mol), 50% aqueous sodium hydroxide solution (5 ml), benzene (10 ml) and 0.5 mmol of compound 1. The mixture was stirred at 60°-70° C. for 5 hours, then cooled to room temperature and diluted with water (10 ml). The organic layer was separated, washed with diluted hydrochloric acid, water and dried over anhydrous magnesium sulphate. The solvent and excess of benzyl chloride were removed under vacuo and the residue was chromatographed on silica gel using n-hexane to give the N-benzylindole (70%), m.p.: 43°-45° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with diluted hydrochloric acid, water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customThe solvent and excess of benzyl chloride were removed under vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-dafa14578f1442fc9748ebdc4ce457cd
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

Loading…