Indole → 1-(4-Chlorobenzyl)-1h-indole

HRID 902090Notes

Reaction equation

HRID 902090 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.O>CS(C)=O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 9671631-(4-Chlorobenzyl)-1h-indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 5.86 g (0.05 mol) of indole in 25 ml of DMSO is added to a mixture of 1.32 g of sodium hydroxide (0.055 mol, suspension in mineral oil) in 50 ml of dimethyl sulfoxide. The mixture is heated at 60° C. for 1.3 hours and then allowed to cool, and 17.7 g (0.11 mol) of 4-chlorobenzyl chloride are added dropwise. The solution is heated at 60° C., allowed to stand overnight and then poured with stirring into 200 ml of water. The mixture is extracted repeatedly with a total of 75 ml of CH2Cl2, the organic phase is dried with anhydrous sodium sulfate and filtered and the filtrate is concentrated under reduced pressure.

Workup

  1. temperatureto cool
  2. temperatureThe solution is heated at 60° C.
  3. additionpoured
  4. extractionThe mixture is extracted repeatedly with a total of 75 ml of CH2Cl2
  5. dry with materialthe organic phase is dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3fb2070bc6c475f9b2f84b09d0986a5
Source dataset
uspto-grants-2008_04
Patent number
US07365081B2

Reaction notes

Loading…