Oxalic Acid → 2-(4-Aminophenyl)-3-[4-(2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

HRID 1595925Notes

Reaction equation

HRID 1595925 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[C:18]4[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=4[S:20][C:21]=3[C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=3)=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C(O)=O>C1COCC1>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[S:20][C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[C:17]=2[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:10][CH:11]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 224627242-(4-Aminophenyl)benzo[b]thiophene-3-yl 4-[2-(1-pyrrolidinyl)ethoxy]phenyl ketone

Product 1

HCID 224627922-(4-Aminophenyl)-3-[4-(2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiopheneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By essentially following the conditions described in Preparation 2, Part D, the free base of the title compound was prepared as an oil from 2-(4-aminophenyl)benzo[b]thiophene-3-yl 4-[2-(1-pyrrolidinyl)ethoxy]phenyl ketone (Part C) in 85% yield following MPLC (SiO2; 30% then 40% THF with 5% TEA in hexanes). The product was converted to the dioxalate salt using two molar equivalents of oxalic acid and a similar procedure to that of Preparation 2-H, above.

Workup

  1. customdescribed in Preparation 2, Part D
  2. customa similar procedure to that of Preparation 2-H

Sources & evidence

ORD record
ord-677ffc5a1cf34d0c8b1bd8b36e37e704
Source dataset
uspto-grants-2001_09
Patent number
US06288105B1

Reaction notes

Loading…