Acetone → 2-[[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol oxalate

HRID 1007916Notes

Reaction equation

HRID 1007916 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]([CH3:20])[CH:16]([CH3:19])[CH2:17][OH:18])[CH:8]=[CH:9][C:2]1=2.[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].CC(C)=O>C(OCC)(=O)C>[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23].[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]([CH3:20])[CH:16]([CH3:19])[CH2:17][OH:18])[CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 3

HCID 180AcetoneHCID 971Oxalic AcidHCID 226662802-[[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol

Product 1

HCID 226664592-[[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol oxalateYield 98.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In 0.9 mL of ethyl acetate is dissolved 0.18 g of 2-{[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-(methyl)amino}-1-propanol, to which is added 2 mL of a solution of 0.055 g of oxalic acid in ethyl acetate. Then, 1 ml of acetone is added, and the resulting mixture is stirred at ambient temperature for 3.5 hours. The deposited crystal is collected by filtration, washed with ethyl acetate and dried to obtain 0.23 g of 2-[[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl](methyl)amino]-1-propanol oxalate.

Workup

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

Sources & evidence

ORD record
ord-25ea1118fa994fa68fc41dbdde9d0a7c
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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