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

HRID 7446Notes

Reaction equation

HRID 7446 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

In 3.0 mL of ethyl acetate was dissolved 0.71 g of 1-{2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl}-3-pyrrolidinamine, and to the solution was added a solution of 0.44 g of oxalic acid in 4.0 mL of ethyl acetate. The resulting mixture was stirred at room temperature for 1 hour and then at 5° C. for 1 hour. The crystals precipitated were collected by filtration, washed with ethyl acetate and then dried to obtain 1.03 g of 1-{2-[2-(1-benzothiophen-5-yl)ethoxy]ethyl}-3-pyrrolidinamine dioxalate as colorless crystals.

Workup

  1. waitat 5° C. for 1 hour
  2. customThe crystals precipitated
  3. filtrationwere collected by filtration
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-2d4bc93aa5fa4c8bb1255f36b8f6217a
Source dataset
uspto-grants-2006_08
Patent number
US07087594B2

Reaction notes

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