Pyridine → N-(4-methoxyphenyl)-2-[[1-(4-pyridyl)piperidin-4-ylcarbonyl]amino]benzamide

HRID 427641Notes

Reaction equation

HRID 427641 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:15][CH2:14][CH:10]([C:11]([OH:13])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24].N1C=CC=CC=1>ClCCl>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:23](=[O:24])[C:22]2[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=2[NH:20][C:11]([CH:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:15][CH2:14]2)=[O:13])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 4788202-amino-N-(4-methoxyphenyl)benzamideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acid

Product 1

HCID 18174545N-(4-methoxyphenyl)-2-[[1-(4-pyridyl)piperidin-4-ylcarbonyl]amino]benzamideYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of N-(4-pyridyl)isonipecotic acid (0.2 g, 1 mmol) in dichloromethane (70 mL) was added thionyl chloride (0.11 mL, 1.5 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was dissolved in dichloromethane (10 mL) and added to a stirred solution of 2-amino-N-(4-methoxyphenyl)benzamide (0.186 g, 0.77 mmol) and pyridine (0.19 g, 0.85 mmol) in dichloromethane (25 mL). After stirring for 72 h, the solution was transferred to a separatory funnel and washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was suspended in a mixture of diethyl ether and hexanes, sonicated, and filtered. The resulting solid was washed with diethyl ether and dried in vacuo to give 0.10 g (30%) of the title compound as a pale tan solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (10 mL)
  3. stirringAfter stirring for 72 h
  4. customthe solution was transferred to a separatory funnel
  5. washwashed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe residue was suspended in a mixture of diethyl ether and hexanes
  10. customsonicated
  11. filtrationfiltered
  12. washThe resulting solid was washed with diethyl ether
  13. customdried in vacuo

Sources & evidence

ORD record
ord-27326af7d0fb49aea7e4c1d4861ee8dd
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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