Fumaric Acid → HCID 22666499, compound

HRID 1007924Notes

Reaction equation

HRID 1007924 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH3:19])[CH2:16][CH2:17][OH:18])[CH:8]=[CH:9][C:2]1=2.[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>C(O)C>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]([CH3:19])[CH2:16][CH2:17][OH:18])[CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 22666261HCID 22666261, compound

Product 1

HCID 22666499HCID 22666499, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 mL of ethanol is dissolved 12.69 g of 2-{[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl](methyl)-amino}-1-ethanol. Then, 5.01 g of fumaric acid is added to the solution and heated. The solvent is distilled off under reduced pressure, 100 mL of acetone and 100 mL of diethyl ether are added to the residue, and the mixture thus obtained is stirred at ambient temperature for 2 hours. After stirring the mixture at 5° C. for an additional one hour, the deposited crystal is collected by filtration, washed with 1:1 mixture of diethyl ether and acetone, and dried to obtain 15.03 g of 2-{[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino}-1-ethanol fumarate.

Workup

  1. temperatureheated
  2. distillationThe solvent is distilled off under reduced pressure, 100 mL of acetone and 100 mL of diethyl ether
  3. additionare added to the residue
  4. customthe mixture thus obtained
  5. stirringAfter stirring the mixture at 5° C. for an additional one hour
  6. filtrationthe deposited crystal is collected by filtration
  7. washwashed with 1:1 mixture of diethyl ether and acetone
  8. customdried

Sources & evidence

ORD record
ord-6893a3fec8c64ec0b447ed0d0544ed42
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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