HCID 54478803, compound → HCID 54111482, compound

HRID 362929Notes

Reaction equation

HRID 362929 reaction equation
[CH2:1]([NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>C(O)(=O)C.O=[Pt]=O>[CH2:1]([NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[C:13]([NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 54478803HCID 54478803, compound

Product 1

HCID 54111482HCID 54111482, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Step 1): A mixture of 2-(N'-n-heptylureido)-N-(pyridin-3-yl)benzamide obtained in the Example 34 (5.0 g, 14 mmol) and PtO2 in acetic acid (70 ml) was stirred at 40° C. under hydrogen atmosphere (50 psi) for 17 hours and then filtered. The filtrate was neutralized with 30% NaOH solution, extracted with ethyl acetate and washed with saturated NaHCO3 solution. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (20% methanol and 0.8% NH4OH in dichloromethane) to give 2-(N'-n-heptylureido)-N-(piperidin-3-yl)benzamide (83.8%): mp 165° C.

Workup

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (20% methanol and 0.8% NH4OH in dichloromethane)

Sources & evidence

ORD record
ord-20be24091fce4045926f430bb79d45da
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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