Benzoylhydrazine → HCID 67109702, compound

HRID 222236Notes

Reaction equation

HRID 222236 reaction equation
N1C=CC=C([O:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[O:9])C=1.O[N:20]1[C:24]2C=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.[CH:29]1[CH:34]=[CH:33][C:32]([C:35]([NH:37][NH2:38])=[O:36])=[CH:31][CH:30]=1.C(N=C=NCCCN(C)C)C>O.C(Cl)(Cl)Cl.C(Cl)Cl>[N:20]1[CH:26]=[CH:27][CH:28]=[C:23]([CH:15]2[CH2:14][CH:13]([C:16]([NH:38][NH:37][C:35](=[O:36])[C:32]3[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=3)=[O:18])[CH2:12][CH2:11][N:10]2[C:8]([OH:7])=[O:9])[CH:24]=1

Participants

8

Reactant 4

HCID 11955BenzoylhydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 574218421-[(Pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acid

Product 1

HCID 67109702HCID 67109702, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-[(pyridin-3 yloxy)carbonyl]piperidine-4-carboxylic acid (1.5 g) and DCM (15 mL) were added 1-hydroxybenzotriazole (HOBt) (0.85 g), benzohydrazine (0.86 g), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (WSC) hydrochloride (1.21 g), followed by stirring at room temperature for about 15 hours. To the reaction liquid were added chloroform and water, and the organic phase was separated. The organic phase was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10). To the purified product were added diisopropyl ether and methanol, and the resulting solid was collected by filtration and dried under reduced pressure to obtain pyridin-3-yl 4-[(2-benzoylhydrazino)carbonyl]piperidine-1-carboxylic acid (1.22 g).

Workup

  1. customTo the reaction liquid
  2. customthe organic phase was separated
  3. washThe organic phase was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10)
  7. additionTo the purified product were added diisopropyl ether and methanol
  8. filtrationthe resulting solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-30924eb689ba4c4084f2e05530f6d999
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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