Pyridine → HCID 19896745, compound

HRID 1196879Notes

Reaction equation

HRID 1196879 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH:19]2[CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[NH3:2].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH2:20][CH:19]2[CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

7

Reactant 3

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 10222149HCID 10222149, compound

Product 2

HCID 222AmmoniaHCID 19896745HCID 19896745, compoundYield 148.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamyl chloride (66 mg) was added to a stirred solution of 1-[(3,4-dichlorophenyl)acetyl]-2-(1-pyrrolidinylmethyl)piperazine (200 mg), pyridine (53 mg) and 4-dimethylaminopyridine (5 mg) in dry dichloromethane at 0° for 4.5 h. The reaction mixture was washed with aqueous 2N sodium carbonate solution (2×10 ml), dried and evaporated to give an oil, which was purified by flash column chromatography eluting with dichloromethane:methanol:0.880 NH3 (200:8:1) to give the title compound as an oil (195 mg).

Workup

  1. washThe reaction mixture was washed with aqueous 2N sodium carbonate solution (2×10 ml)
  2. customdried
  3. customevaporated
  4. customto give an oil, which
  5. customwas purified by flash column chromatography
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9b0f5eb2012e467cb004b38429eddf70
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

Loading…