Morpholine → 4-(5-Bromopyridin-3-yl)morpholine

HRID 2202649Notes

Reaction equation

HRID 2202649 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN1C(=O)CCC1.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1>C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:20]=[C:19]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:18]=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 13387N-methyl-2-pyrrolidoneHCID 693693,5-Dibromopyridine

Product 1

HCID 467396144-(5-Bromopyridin-3-yl)morpholineYield 19.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of morpholine (3.67 g, 4.23 mmol), NMP (2 mL) and toluene (4 mL) was added 3,5-dibromopyridine (1.00 g, 4.20 mmol) and the mixture was heated under microwave conditions at 180° C. for 1 h. The solution was partitioned between DCM and water, the organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography eluting with (EtOAc: PE=1:5). (200 mg, yield 19.5%) MS (ESI+) e/z: 243.0 [M+1]+ LCMS.

Workup

  1. customThe solution was partitioned between DCM and water
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography
  7. washeluting with (EtOAc: PE=1:5)

Sources & evidence

ORD record
ord-de51c1141a4e493ca5ab435cdefe3198
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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