Oxalyl chloride → n-(4-{1-[Bis-(2-chlorphenyl)-methyl]-piperidin-4-yl}-butyl)-3-(pyridin-3-yl)-acrylamid

HRID 1280763Notes

Reaction equation

HRID 1280763 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)=O.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[Cl:43])[N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH2:28][CH2:27]1>>[Cl:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[Cl:18])[N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:9](=[O:11])[CH:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 184257064-{1-[Bis(2-chlorophenyl)methyl]-piperidin-4-yl}-butylamine

Product 1

HCID 53941497n-(4-{1-[Bis-(2-chlorphenyl)-methyl]-piperidin-4-yl}-butyl)-3-(pyridin-3-yl)-acrylamid

Procedure

Batch size: 1.6 g (10.7 mmol) 3-(3-pyridyl)-acrylic acid, 1.9 g (15.0 mmol) oxalyl chloride and 3.9 g (10.0 mmol) 4-{1-[bis-(2-chlorophenyl)-methyl]-piperidine-4-yl}-butylamine. In the purification, chromatographic purification is done twice over silica gel with CHCl3/CH3OH (97/3 and 97/3 to 95/5) and crystallization is from 25 ml acetic acid after drawing off the solvent. Colorless crystals with a MP of 129-131° C. were recovered; yield: 0.6g (11%).

Workup

  1. customIn the purification, chromatographic purification
  2. customis done twice over silica gel with CHCl3/CH3OH (97/3 and 97/3 to 95/5) and crystallization
  3. customColorless crystals with a MP of 129-131° C. were recovered

Sources & evidence

ORD record
ord-1ec57c48f48c4a81ae13a4ac061e4461
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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