Water → 4-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one

HRID 2102872Notes

Reaction equation

HRID 2102872 reaction equation
[N:1]1([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:6][CH2:5][C:4](=O)[CH2:3][C:2]1=[O:8].[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH2:18].O>CC1CCCO1>[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH:18][C:4]1[CH2:5][CH2:6][N:1]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 111232,4-DichloroanilineHCID 22038474[1,1']Bipiperidinyl-2,4-dione

Product 1

HCID 442497124-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

1,1′-bipiperidine-2, 4-dione (1,000 g, 4,739 mmol) and 2,4-dichloroaniline (0.921 g, 5.687 mmol) were dissolved in 2-methyltetrahydrofuran (10 ml) and the reaction mixture was boiled under reflux for 22 h whilst the water formed was removed using a Dean and Stark apparatus. Upon cooling to rt the product precipitated and was collected by filtration to yield a white solid (1.490 g, 92%).

Workup

  1. customformed
  2. customwas removed
  3. customprecipitated
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b8ee5bc764b549248da99b0bb401eb90
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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