1-(4-(2-(4-aminophenoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone → 1-(4-(2-(4-Aminophenoxy)pyridin-3-yl)piperidin-1-yl)ethanone

HRID 473694Notes

Reaction equation

HRID 473694 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[C:12]([C:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH:14]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[C:12]([CH:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 593739281-(4-(2-(4-aminophenoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

Product 1

HCID 593739391-(4-(2-(4-Aminophenoxy)pyridin-3-yl)piperidin-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(4-(2-(4-aminophenoxy)pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.98 g, 3.17 mmol) in ethanol (16 mL) was added palladium, 10 wt. % on carbon (0.1 g, 0.094 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 18 h. The reaction mixture was filtered via a pad of Celite, and the filtrate was concentrated in vacuo and chromatographed via flash column chromatography (20% to 80% EtOAc/Hexanes) to give 1-(4-(2-(4-aminophenoxy)pyridin-3-yl)piperidin-1-yl)ethanone as a light tan solid. MS (ESI, pos. ion) m/z: 312.0 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered via a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed via flash column chromatography (20% to 80% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b56748327584449c8830bebfd4b38b7b
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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