1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 10221262, compound

HRID 1007879Notes

Reaction equation

HRID 1007879 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][OH:14])[CH:10]=[CH:11][C:4]1=2.Cl.Cl[CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH2:12][CH2:13][O:14][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:10]=[CH:11][C:4]1=2

Participants

7

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium HydroxideHCID 119833712-(1-Benzothiophen-5-yl)ethan-1-ol

Product 1

HCID 10221262HCID 10221262, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

In a mixture of 10 mL of 50% (W/V) aqueous solution of sodium hydroxide and 2 mL of toluene is suspended 2.00 g of 2-benzo[b]thiophen-5-yl-1-ethanol. To the suspension are added 2.51 g of N-(2-chloroethyl)-N,N-diethylamine hydrochloride and 0.38 g of tetra-n-butylammonium hydrogen sulfate, and the resulting mixture is heated under reflux for one hour. Water and toluene are added to the reaction mixture, and the organic layer is separated. The organic layer is washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent:chloroform:methanol=10:1) to obtain 3.10 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-diethylamine as an oily product.

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for one hour
  3. customthe organic layer is separated
  4. washThe organic layer is washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography (eluent:chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a9cec6b8a27f48128fe3cabf22881587
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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