1-Benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridine → 3-(Piperidin-4-yl)pyridine

HRID 2256042Notes

Reaction equation

HRID 2256042 reaction equation
C(OC([N:11]1[CH:16]=[CH:15][CH:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[CH:18]=1

Participants

5

Reactant 2

HCID 190291131-Benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 46903903-(Piperidin-4-yl)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridine (0.714 in ethanol (50 mL) was treated with 10% palladium on carbon (0.1 g) and hydrogenated under a hydrogen atmosphere at room temperature and 3.44 bar for 16 hours. The reaction mixture was filtered through diatomaceous earth to remove the catalyst, and the resulting filtrate was evaporated to afford the piperidine (0.393 g); NMR (CDCl3): 1.7 (m, 4), 2.8 (m, 4), 3.2 (m, 2), 7.3 (m, 1), 7.5 (m, 1), 8.5 (m, 2); MS: m/z=162(M+1).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customto remove the catalyst
  3. customthe resulting filtrate was evaporated

Sources & evidence

ORD record
ord-64a60d14893e4aad8b0b7d8105db3be9
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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