Hydrochloric Acid → HCID 22666526, compound

HRID 1007881Notes

Reaction equation

HRID 1007881 reaction equation
CS(O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[CH:12]=1)(=O)=O.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21].O.Cl>CN(C)C=O.C(OCC)(=O)C>[O:15]1[C:14]2[CH:18]=[CH:19][C:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][N:22]([CH2:23][CH3:24])[CH2:20][CH3:21])=[CH:12][C:13]=2[O:17][CH2:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8021DiethylamineHCID 22666423HCID 22666423, compound

Product 1

HCID 22666526HCID 22666526, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 3 mL of N,N-dimethylformamide is dissolved 1.00 g of 2-[2-(1,3-benzodioxol-5-yl)ethoxy]ethyl methanesulfonate. To the solution is added 2.54 g of diethylamine. The resulting mixture is stirred at 100° C. for 2 hours in an ampoule. After cooling, the reaction mixture is introduced into a mixture of water and ethyl acetate, pH is adjusted to 1.0 with 2 mol/L hydrochloric acid, and the aqueous layer is separated. Ethyl acetate is added to the aqueous layer, pH is adjusted to 9.5 with sodium carbonate, 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=20:1 to 10:1) to obtain 0.75 g of N-{2-[2-(1,3-benzodioxol-5-yl)ethoxy]ethyl}-N,N-diethylamine as an oily product.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous layer is separated
  3. additionEthyl acetate is added to the aqueous layer
  4. customthe organic layer is separated
  5. washThe organic layer is washed successively with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customthe residue is purified by column chromatography (eluent:chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-b28af09e3c094da4ae54029f13d78937
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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