1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one O-benzyl-oxime → 1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamine

HRID 451431Notes

Reaction equation

HRID 451431 reaction equation
C(O[N:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]2[O:17][C:18]([CH3:21])=[N:19][N:20]=2)[CH2:12][CH2:11]1)C1C=CC=CC=1>N.CO.[Pd]>[CH3:21][C:18]1[O:17][C:16]([N:13]2[CH2:12][CH2:11][CH:10]([NH2:9])[CH2:15][CH2:14]2)=[N:20][N:19]=1

Participants

5

Reactant 1

HCID 866567051-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one O-benzyl-oxime

Product 1

HCID 673446221-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-ylamineYield 109.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one O-benzyl-oxime (2.32 g, 8.1 mmol)) in 7 M NH3 solution in MeOH (40.5 mL) was hydrogenated under an atmosphere of hydrogen in the presence of Palladium on charcoal (10%, 464 mg). The catalyst was filtered off and washed with MeOH. The filtrate was concentrated under reduced pressure to yield the title compound (1.61 g, 100%) as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-010aa155aa764b299b148d6d80602e0e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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