Sodium Iodide → HCID 23501285, compound

HRID 1835918Notes

Reaction equation

HRID 1835918 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl.Cl[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24]>CC(=O)CC>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 754211H-indol-4-olHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 23501285HCID 23501285, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 100 mL round-bottomed flask equipped with magnetic stirrer and a reflux condenser was charged with 2-butanone (30 mL), 4-hydroxy-1H-indole (1.197 g, 0.009 mol), potassium carbonate (44.71 g, 0.036 mol) and sodium iodide (0.137 g, 0.0009 mol). To this mixture was added 2-chloro-N,N-dimethylethylamine hydrochloride (1.43 g, 0.010 mol). The reaction mixture was brought to reflux and stirred for 24 hours. The solvent was removed in vacuo and the resulting crude residue was dissolved in 60 mL of ethyl acetate and the solution was washed sequentially with water (3×45 mL) and brine (1×45 mL). The aqueous fractions were extracted with ethyl acetate (2×20 mL) and the combined organic fractions were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (95:4.9:0.1 dichloromethane/methanol/ammonium hydroxide) to afford 2-(1H-indol-4-yloxy)ethyl dimethylamine as a transparent pale blue oil (1.322 g, 72%). MS: (M+H)+=205.4.

Workup

  1. customA 100 mL round-bottomed flask equipped with magnetic stirrer and a reflux condenser
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting crude residue was dissolved in 60 mL of ethyl acetate
  5. washthe solution was washed sequentially with water (3×45 mL) and brine (1×45 mL)
  6. extractionThe aqueous fractions were extracted with ethyl acetate (2×20 mL)
  7. dry with materialthe combined organic fractions were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (95:4.9:0.1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-2e541101093144c4aa2b3d95bc3cd6f7
Source dataset
uspto-grants-2004_08
Patent number
US06774241B2

Reaction notes

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