Isopropyl iodide → HCID 10130811, compound

HRID 2084042Notes

Reaction equation

HRID 2084042 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][CH:9]=1)[CH3:5].I[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[NH3:4].[CH3:3][N:4]([CH2:6][CH2:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][N:14]2[CH:18]([CH3:20])[CH3:19])=[CH:10][CH:9]=1)[CH3:5]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 10176453HCID 10176453, compound

Product 2

HCID 222AmmoniaYield 7%HCID 10130811HCID 10130811, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (12.7 mg, 0.531 mmol) was added to an ice-cooled solution 6-(2-(N,N-Dimethylamino)ethyl)-1H-indole (50 mg, 0.265 mmol) in DMF (1 ml). After stirring for 1 h at 0° C., 2-iodopropane (52.9 μL, 0.530 mmol) was added and the mixture stirred at 100° C. overnight. The reaction mixture was then partitioned between water and dichloromethane, the organic layer washed sequentially with water and brine, dried over sodium sulfate and the solvent was removed in vacuo. Flash chromatography (silica gel, 7% methanolic ammonia in dichloromethane) gave the title product (10 mg, 16%).

Workup

  1. stirringthe mixture stirred at 100° C. overnight
  2. customThe reaction mixture was then partitioned between water and dichloromethane
  3. washthe organic layer washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dab7dfce4e2d4f548d77cff5ce0b127c
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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