Oxalic Acid → N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine oxalate

HRID 1007918Notes

Reaction equation

HRID 1007918 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][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][C:17]#[CH:18])[CH:8]=[CH:9][C:2]1=2.[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28]>C(OCC)(=O)C>[C:26]([OH:31])(=[O:30])[C:27]([OH:29])=[O:28].[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][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:16][C:17]#[CH:18])[CH:8]=[CH:9][C:2]1=2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 22666539N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine

Product 1

HCID 22666558N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine oxalateYield 74.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 1 mL of ethyl acetate is dissolved 0.67 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine, to which is added 2.3 mL of a solution of 0.26 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 0.63 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-benzyl-N-(2-propynyl)amine oxalate.

Workup

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

Sources & evidence

ORD record
ord-74857256949c4694b0fb450daf29f9e7
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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