HCID 53904510, compound → HCID 53783949, compound

HRID 362926Notes

Reaction equation

HRID 362926 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 53904510HCID 53904510, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53783949HCID 53783949, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step 1): 10% Pd/C was added to a solution of the N-(1-benzylpiperidin-4yl)-2-(N'-n-heptylureido)benzamide (1.4 g, 3.1 mmol) obtained in Example 41 in methanol (25 ml) under nitrogen. The mixture was shaken under 50 psi hydrogen pressure for 5 hours, and then filtered under nitrogen. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (50% methanol and 0.8% NH4OH in dichloromethane) to give N-(piperidin-4-yl)-2-(N'-n-heptylureido)benzamide: 48.4%: mp 159° C.

Workup

  1. filtrationfiltered under nitrogen
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (50% methanol and 0.8% NH4OH in dichloromethane)

Sources & evidence

ORD record
ord-990a66254f79419396dbf2bb2d2e2fed
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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