Chlorobenzene → HCID 13747117, compound

HRID 974276Notes

Reaction equation

HRID 974276 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=2[Cl:18])[C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:8]([CH3:23])[NH:7][C:6]=1[CH2:24][CH2:25]N(C)C)=[O:4].[CH3:29][C:30]1[NH:31][CH:32]=[CH:33][N:34]=1.N12CCCN=C1CCCCC2.ClC1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:18][C:12]1[C:13]([Cl:17])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:10]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([CH2:24][CH2:25][N:31]2[CH:32]=[CH:33][N:34]=[C:30]2[CH3:29])[NH:7][C:8]([CH3:23])=[C:9]1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 127492-MethylimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67928302HCID 67928302, compound

Product 1

HCID 13747117HCID 13747117, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-(2,3-dichlorophenyl)-1,4-dihydro-6-methyl-2-(2-dimethylaminoethyl)pyridine 3,5-dicarboxylic acid dimethyl ester (2.14 g, 5mmol), 2-methylimidazole (1.64 g, 20mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.75 g, 5mmol) and chlorobenzene (50ml) was heated at reflux for 24hours. The solution was cooled, diluted with chloroform (25ml), washed with water (100ml), dried and evaporated. The residue was chromatographed on silica gel (50 g, Act I) using chloroform-methanol as eluent to give the title compound. This was suspended in methanol (10ml) and acidified by addition of maleic acid (0.5 g, 5% excess) to give a clear solution which was then diluted with ether (10ml) to precipitate the crystalline maleate salt 1.65 g mp 197°-198°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24hours
  3. temperatureThe solution was cooled
  4. washwashed with water (100ml)
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (50 g, Act I)

Sources & evidence

ORD record
ord-e1d8f13c2014477794b27012bf839940
Source dataset
uspto-grants-1991_11
Patent number
US05068337

Reaction notes

Loading…