Oxalic Acid → 1-{2-[2-(1-Benzothiophen-5-yl)ethoxy]ethyl}-3-pyrrolidinamine dioxalate

HRID 597819Notes

Reaction equation

HRID 597819 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16]3)=[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].[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 21990143HCID 21990143, compound

Product 1

HCID 858267051-{2-[2-(1-Benzothiophen-5-yl)ethoxy]ethyl}-3-pyrrolidinamine dioxalateYield 89.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

0.71 g of 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-pyrrolidinamine was dissolved in 3.0 ml of ethyl acetate. Thereafter, 4.0 ml of an ethyl acetate solution containing 0.44 g of oxalic acid was added to the obtained solution, and the obtained 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, washed with ethyl acetate, and then dried, so as to obtain 1.03 g of an achromatic crystal, 1-(2-(2-(1-benzothiophene-5-yl)ethoxy)ethyl)-3-pyrrolidinamine dioxalate.

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. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-38c5ff8065e8407995cc02e55155403b
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Reaction notes

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