3-[3-(Ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester → (2-Methyl-5-piperidin-3-ylphenylamino)acetic acid ethyl ester

HRID 1269549Notes

Reaction equation

HRID 1269549 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([NH:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:18]=2)[CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][NH:24][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)[CH:22]=[CH:21][C:20]=1[CH3:23])[CH3:30]

Participants

4

Reactant 1

HCID 688848003-[3-(Ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 68883656(2-Methyl-5-piperidin-3-ylphenylamino)acetic acid ethyl esterYield 123.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A 100 mL Parr bottle was charged with 30 mg of 10% palladium on carbon (50% water) and covered with 10 mL ethanol. 3-[3-(ethoxycarbonylmethyl-amino)-4-methyl-phenyl]-piperidine-1-carboxylic acid benzyl ester (152 mg, 0.37 mmol) was dissolved in 10 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 45 psi for 2 h. The catalyst was filtered through a celite plug. The filter cake was washed with 30 mL ethanol and the filtrate concentrated under reduced pressure to yield 126 mg (100%) of (2-methyl-5-piperidin-3-yl-phenylamino)-acetic acid ethyl ester as a clear oil.

Workup

  1. additionadded to the catalyst suspension
  2. filtrationThe catalyst was filtered through a celite plug
  3. washThe filter cake was washed with 30 mL ethanol
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcc6a5b02dcd4df4985c1e3b406c5c78
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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