Oxalic Acid → N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine oxalate

HRID 1007894Notes

Reaction equation

HRID 1007894 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]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH:8]=[CH:9][C:2]1=2.[C:22]([OH:27])(=[O:26])[C:23]([OH:25])=[O:24]>C(OCC)(=O)C>[C:22]([OH:27])(=[O:26])[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]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 22666418N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine

Product 1

HCID 22666417N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine oxalateYield 72.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 1 mL of ethyl acetate is dissolved 0.60 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine, to which is added 2 mL of a solution of 0.18 g of oxalic acid in ethyl acetate. The resulting mixture is stirred at ambient temperature for 2 hours. The deposited crystal is collected by filtration, washed with ethyl acetate and dried to obtain 0.56 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N,N-dipropylamine oxalate.

Workup

  1. filtrationThe deposited crystal is collected by filtration
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-0710a4ff2eac4ab7bde31737691e1bf6
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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