Oxalic Acid → 1-{2-[2-(1-Benzothiophen-6-yl)ethoxy]ethyl}-3-pyrrolidinol oxalate

HRID 597815

Reaction equation

HRID 597815 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>C(OCC)(=O)C>[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 219900201-{2-[2-(1-Benzothiophen-6-yl)ethoxy]ethyl}-3-pyrrolidinol

Product 1

HCID 219901241-{2-[2-(1-Benzothiophen-6-yl)ethoxy]ethyl}-3-pyrrolidinol oxalateYield 66.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.48 g of 1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol was dissolved in 2.0 ml of ethyl acetate. Thereafter, 2.8 ml of an ethyl acetate solution containing 0.15 g of oxalic acid was added to the obtained solution, and the mixture was stirred at a room temperature for 1 hour and then at 5° C. for 1 hour. Thereafter, precipitated crystals were collected by filtration and were then washed with ethyl acetate, followed by drying, so as to obtain 0.42 g of an achromatic crystal, 1-(2-(2-(1-benzothiophene-6-yl)ethoxy)ethyl)-3-pyrrolidinol oxalate.

Workup

  1. additionwas added to the obtained solution
  2. waitat 5° C. for 1 hour
  3. customThereafter, precipitated crystals
  4. filtrationwere collected by filtration
  5. washwere then washed with ethyl acetate
  6. customby drying

Sources & evidence

ORD record
ord-c785b7893c5d484194005ca6367e8eef
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Linked notes

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