Water → HCID 10462425, compound

HRID 1007895Notes

Reaction equation

HRID 1007895 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH:9]=1.[CH3:17][NH:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[S:12]1[CH:13]=[CH:14][C:10]2[CH:9]=[C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:18]([CH3:17])[CH2:19][CH2:20][OH:21])[CH:16]=[CH:15][C:11]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

Product 1

HCID 10462425HCID 10462425, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In 6 mL of N,N-dimethylformamide is dissolved 0.80 g of 5-[2-(3-chloropropyloxy)ethyl]benzo[b]-thiophene, to which are added 0.51 mL of 2-(methylamino)ethanol and 0.87 g of potassium carbonate. The mixture is stirred at 80° C. for 3 hours. The reaction mixture is introduced into a mixture of water and ethyl acetate. The organic layer is separated, washed 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). Thus, 0.59 g of 2-{[3-(2-benzo[b]thiophen-5-ylethoxy)propyl]-(methyl)amino]-1-ethanol is obtained as an oily product.

Workup

  1. customThe organic layer is separated
  2. washwashed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customthe residue is purified by column chromatography (eluent: chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-96b64a41c607495883c81ef1f8893c3b
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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