Acetic Acid → HCID 59714958, compound

HRID 2223883Notes

Reaction equation

HRID 2223883 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3([C:23]([O:25]CC4C=CC=CC=4)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.C(O)(=O)C>C(O)C.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59714861HCID 59714861, compound

Product 1

HCID 59714958HCID 59714958, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl 1-[2-[4-(5-methylpiridin-2-yl-amino)piperidin-1-yl]ethyl]cyclohexanecarboxylate (160 mg, 0.37 mmol) in ethanol (16 mL) was added 10% palladium carbon (80 mg) at room temperature. The mixture was stirred at room temperature under hydrogen atmosphere for 24 hours. Acetic acid was added to the mixture, and it was filtered with Celite and concentrated under reduced pressure. Methanol and diethyl ether were added to the residue, and the solution was stirred under ice cooling for 1 hour. The crystals were recovered by filtration to give the title compound (100 mg).

Workup

  1. filtrationwas filtered with Celite
  2. concentrationconcentrated under reduced pressure
  3. additionMethanol and diethyl ether were added to the residue
  4. stirringthe solution was stirred under ice cooling for 1 hour
  5. filtrationThe crystals were recovered by filtration

Sources & evidence

ORD record
ord-aba4ca2111ae435789f9ae79a3c549ba
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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