HCID 19029125, compound → 4-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidine

HRID 2256035Notes

Reaction equation

HRID 2256035 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]([CH3:22])=[N:20][N:21]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH3:22][C:19]1[O:18][C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[N:21][N:20]=1

Participants

5

Reactant 2

HCID 19029125HCID 19029125, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 190291464-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidineYield 981.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(5-methyl-1,3,4-oxadiazol-2-yl)piperidine (0.18 g) in ethanol (5 mL) was hydrogenated over 10% palladium on carbon (0.050 g) at a hydrogen pressure of 1 bar for 2 hours. The catalyst was then removed by filtration through diatomaceous earth, the filter cake was washed with ethanol and the solvent evaporated to afford the piperidine as a white crystalline solid (0.98 g); mp 64°-66° C.; NMR (CDCl3): 3.17 (m, 2), 2.98 (m, 1), 2.75 (dr,2, J=2.6, 12.0), 2.51 (s, 3), 2.01 (m, 2), 1.75 (m, 2); MS: m/z=196(M+1+28).

Workup

  1. customThe catalyst was then removed by filtration through diatomaceous earth
  2. washthe filter cake was washed with ethanol
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-e6ce7915afab43cda9ddd22c7cd62fd1
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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