N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl]amine → N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylcarbonyl)amine

HRID 429822Notes

Reaction equation

HRID 429822 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([N:12]([C:15]([CH:17]2[CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)=[O:16])[CH2:13][CH3:14])[CH3:11])=[CH:5][CH:4]=1>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([N:12]([C:15]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:16])[CH2:13][CH3:14])[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 18352914N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl]amine

Product 1

HCID 18353004N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylcarbonyl)amineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-[1-(benzyloxycarbonyl)piperidin-4-ylcarbonyl]amine (3.5 grams, 8.3 mmole) and 10% palladium on carbon (0.7 grams) in ethanol (40 ml) was hydrogenated at 22° C. and 50 p.s.i. for 2.5 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to leave N-[2-(4-methoxyphenyl)-1-methylethyl]-N-ethyl-(piperidin-4-ylcarbonyl)amine as a syrup (2.11 grams, 84%), M+H 305.

Workup

  1. customwas hydrogenated at 22° C.
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e69fbdab26dc4199b1dd630b936c326e
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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