4-[3-(Azidomethyl)pyridin-2-yl]morpholine → 1-[2-(Morpholin-4-yl)pyridin-3-yl]methanamine

HRID 2240366Notes

Reaction equation

HRID 2240366 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)=[N+]=[N-]>CO.[Pd]>[N:11]1([C:6]2[C:5]([CH2:4][NH2:1])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 860822534-[3-(Azidomethyl)pyridin-2-yl]morpholine

Product 1

HCID 167903031-[2-(Morpholin-4-yl)pyridin-3-yl]methanamineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Example 115A (0.62 g) in methanol (10 ml) was added Pd/C (0.06 g) under N2 atmosphere. The reaction mixture was stirred at room temperature under H2 atmosphere. After 6 h, the reaction mixture was filtered through celite and concentrated to yield 0.42 g (78%) of product. MS (ESI+) m/z 194 (M+H)+;

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7e593ffd75f6477690926ca5de52bdd4
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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