Methane → 5-Morpholinopyridin-2-amine

HRID 1262290Notes

Reaction equation

HRID 1262290 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C.C(O)C>[OH-].[OH-].[Pd+2].O>[N:10]1([C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[N:9][CH:8]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 297MethaneHCID 702EthanolHCID 29279734-(6-Nitropyridin-3-yl)morpholine

Product 1

HCID 113673465-Morpholinopyridin-2-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 962WaterSolvent

Procedure

Into a round bottom flask, 4-(6-Nitro-pyridin-3-yl)-morpholine (1.67 g, 0.00798 mol), 20% Pd(OH)2/C, 50% wet (10:40:50, Palladium hydroxide:carbon black:Water, 0.350 g, 0.000249 mol), and Ethanol (50 mL, 0.9 mol) were added into a parr bottle. The mixture was evacuated under house vacuum and charged with hydrogen at 35 pSi. The reaction was shaken at room temperature at 35 pSi. The solid was filtered. The solvent was removed under vacuum to afford an off white solid. The solid was triturated with Et2O, Filtered and washed with Et2O to give 5-Morpholin-4-yl-pyridin-2-ylamine as an off white solid (1.01, 70%).

Workup

  1. customThe mixture was evacuated under house vacuum
  2. additioncharged with hydrogen at 35 pSi
  3. filtrationThe solid was filtered
  4. customThe solvent was removed under vacuum
  5. customto afford an off white solid
  6. customThe solid was triturated with Et2O
  7. filtrationFiltered
  8. washwashed with Et2O

Sources & evidence

ORD record
ord-3e4838f6f8064f8a895489cdd335c4a2
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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