Morpholine → 4-(Morpholin-4-yl)pyridin-2-amine

HRID 1848222Notes

Reaction equation

HRID 1848222 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>CC(N(C)C)=O>[O:12]1[CH2:13][CH2:14][N:9]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 219345374-(Morpholin-4-yl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-chloropyridin-2-amine (400 mg, 3.1 mmol) and morpholine (2 mL) in 2 mL of DMA was heated at 200° C. for 5 min in a microwave reactor. LCMS analysis indicated completion of the reaction. The mixture was partitioned between EtOAc and brine, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to give crude 4-morpholinopyridin-2-amine as a yellow solid (350 mg). LCMS (ESI) m/z 180 (M+H)+.

Workup

  1. customcompletion of the reaction
  2. customThe mixture was partitioned between EtOAc and brine
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9daf0ffe0a204f6c8230df2a2f509553
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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