1-benzyl-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine → 4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine

HRID 1380956Notes

Reaction equation

HRID 1380956 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:26]([O:28][CH3:29])=[O:27])([N:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:17])[CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].C(O)(=O)C>[CH3:29][O:28][C:26]([C:11]1([N:14]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15](=[O:17])[CH3:16])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:27]

Participants

5

Reactant 2

HCID 233248381-benzyl-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 233248214-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 12.45 g of 1-benzyl-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine and 250 ml of acetic acid is hydrogenated at room temperature and pressure with 1.5 g of 10% palladium-on-charcoal catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off. The acetic acid is flash evaporated, the residue is dissolved in toulene and stirred with 10 g of anhydrous sodium carbonate. The solid is filtered and the filtrate is flash evaporated to obtain 4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine.

Workup

  1. customis hydrogenated at room temperature
  2. filtrationthe catalyst is filtered off
  3. customevaporated
  4. dissolutionthe residue is dissolved in toulene
  5. filtrationThe solid is filtered
  6. customevaporated

Sources & evidence

ORD record
ord-cbccb428274b419395cd1469a0960944
Source dataset
uspto-grants-1986_04
Patent number
US04584303

Reaction notes

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