Ethanol → HCID 86721006, compound

HRID 524950Notes

Reaction equation

HRID 524950 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:11][CH2:12][N:13]([CH:16]2[CH2:19][O:18][CH2:17]2)[CH2:14][CH:15]=1)([O-])=O.CCO>CCOC(C)=O.[Pd]>[O:18]1[CH2:19][CH:16]([N:13]2[CH2:14][CH2:15][CH:10]([C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[NH2:1])[CH2:11][CH2:12]2)[CH2:17]1

Participants

5

Reactant 2

HCID 702EthanolHCID 86721005HCID 86721005, compound

Product 1

HCID 86721006HCID 86721006, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd on C, wet, Degussa (240 mg, 0.2255 mmol) was added to a stirred solution of 3-nitro-4-[1-(oxetan-3-yl)-3,6-dihydro-2H-pyridin-4-yl]pyridine (614 mg, 2.350 mmol) in EtOAc (20 mL)/EtOH (20 mL). The reaction was placed under an atmosphere of hydrogen and stirred at ambient temperature for 15 hours. The catalyst was removed by filtration through a pad of celite and the filtrate concentrated in vacuo to give the 4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-3-amine as a pale yellow solid (518 mg, 95% Yield). MS (ES+) 234.2.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-260627df7d7244eb8f9733855dff372f
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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