Phenylhydrazine → HCID 53358167, compound

HRID 538755Notes

Reaction equation

HRID 538755 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][C:14](=O)[CH:13]([C:18]([O:20]CC)=O)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:23]1([NH:29][NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC[O-].[Na+].CCO>CCO.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][C:14]3[NH:30][N:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18](=[O:20])[C:13]=3[CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7516PhenylhydrazineHCID 13355956HCID 13355956, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 53358167HCID 53358167, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

In a three-necked flask, under a N2 atmosphere, 0.300 g (0.92 mmol) of ethyl 1-[(4-methyl phenyl)sulfonyl]-4-oxopiperidine-3-carboxylate and 0.099 g (0.92 mmol) of phenyl hydrazine were stirred in 3 mL of EtOH for 1 h at 50° C. HPLC and UPLC-MS analysis revealed the formation of the hydrazone intermediate. After having cooled to room temperature, a solution of EtONa/EtOH—prepared by dissolution of 42 mg (1.84 mmol) of Na in 2 mL of EtOH—was added to the reaction mixture and it was stirred for 1 additional hour at room temperature (reaction monitored by HPLC and UPLC-MS). The reaction mixture was diluted with brine (10 mL) and extracted with ethylacetate (50 mL×3). The combined organic phases were dried over Na2SO4 and evaporated. The crude (400 mg) was purified by silica flash chromatography using ethylacetate/petroleum ether (80/20, gradient to 100% ethylacetate) yielding 84 mg of a white solid as the desired 5-[(4-methylphenyl)sulfonyl]-2-phenyl-1,2,4,5,6,7-hexahydro-3H-pyrazolo[4,3-c]pyridin-3-one (25% yield). 1HNMR (500 MHz, DMSO-d6): 3.95 (s, 3H); 2.64 (t, J=5.5 Hz, 2H); 3.17 (d, J=5 Hz, 2H); 3.30 (m, 2H, hidden by H2O); 7.20 (t, J=7.25 Hz, 1H); 7.40-7.45 (m, 4H); 7.65-7.7 (m, 4H); 11.36 (bs, NH); 370.

Workup

  1. additionwas added to the reaction mixture and it
  2. custom(reaction monitored by HPLC and UPLC-MS)
  3. extractionextracted with ethylacetate (50 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated
  6. customThe crude (400 mg) was purified by silica flash chromatography

Sources & evidence

ORD record
ord-b19d7f00c1b74cd2b9464165dca9869a
Source dataset
uspto-grants-2014_10
Patent number
US08865758B2

Reaction notes

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