Water → 1-(4-Cyanobutyl)-3-methyl-2-(1-imidazolyl)indole

HRID 1719395Notes

Reaction equation

HRID 1719395 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24].O>CN(C)C=O>[C:23]([CH2:22][CH2:21][CH2:20][CH2:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[C:3]1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 794355-BromopentanenitrileHCID 132808392-(1-Imidazolyl)-3-methylindole

Product 1

HCID 202681831-(4-Cyanobutyl)-3-methyl-2-(1-imidazolyl)indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-methyl-2-(1-imidazolyl)-indole (2.0 g) in 12 ml of dimethylformamide is added to a suspension of 0.6 g of 50% sodium hydride (dispersion in mineral oil) in 6 ml of dimethylformamide at 0°. The mixture is stirred at 0° for 0.5 hour and is treated with a solution of 1.8 g of 5-bromovaleronitrile in 4 ml of dimethylformamide. This mixture is stirred at room temperature overnight and is poured into 125 ml of water. This is extracted with 2×50 ml of ethyl acetate, the extract is washed with water and dried over magnesium sulfate to give 1-(4-cyanobutyl)-3-methyl-2-(1-imidazolyl)-indole.

Workup

  1. stirringThis mixture is stirred at room temperature overnight
  2. extractionThis is extracted with 2×50 ml of ethyl acetate
  3. washthe extract is washed with water
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1065f7b8fa594594bebb5d90dddff326
Source dataset
uspto-grants-1985_09
Patent number
US04539410

Reaction notes

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