Oxalyl chloride → N-{2-[2-(4-diphenylmethyl-piperazin-1-yl)-ethoxy]-ethyl}-3-pyridin-3-yl-acrylamide trihydrochloride

HRID 1070747Notes

Reaction equation

HRID 1070747 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=O)[CH:2]=1.C(Cl)(=O)C([Cl:15])=O.[C:18]1([CH:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][NH2:36])[CH2:27][CH2:26]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[ClH:15].[ClH:15].[ClH:15].[C:37]1([CH:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:25]2[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][NH:36][C:9](=[O:11])[CH:8]=[CH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:29][CH2:30]2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 223976322-[2-(4-Diphenylmethyl-piperazin-1-yl)-ethoxy]-ethylamine

Product 1

HCID 69687141N-{2-[2-(4-diphenylmethyl-piperazin-1-yl)-ethoxy]-ethyl}-3-pyridin-3-yl-acrylamide trihydrochloride

Procedure

Batch size: 6.0 g (40 mmol) 3-(3-pyridyl)-acrylic acid, 9.4 ml (110 mmol) oxalyl chloride and 12.4 g (36.5 mmol) 2-[2-(4-diphenylmethyl-piperazin-1-yl)-ethoxy]-ethylamine. The crude product is chromatographically pre-purified over silica gel with CHCl3/CH3OH (98/2 to 95/5). After removal of the solvent, the residue is dissolved in isopropanol and mixed with isopropanolic HCl solution. The mixture is rotated in and the HCl salt is cyrstallized from 50 ml methanol/6 drops diisopropyl ether: Colorless crystals of MP. 157-159° C.; yield 0.6 g (3%).

Workup

  1. customThe crude product is chromatographically pre-purified over silica gel with CHCl3/CH3OH (98/2 to 95/5)
  2. customAfter removal of the solvent
  3. dissolutionthe residue is dissolved in isopropanol
  4. additionmixed with isopropanolic HCl solution
  5. customcrystals of MP. 157-159° C.

Sources & evidence

ORD record
ord-2bb7583f370a4162bc40973415e14a5f
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

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