Morpholine → 6-(Morpholin-4-yl)pyridin-2-amine

HRID 1396874Notes

Reaction equation

HRID 1396874 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>>[N:9]1([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 187718606-(Morpholin-4-yl)pyridin-2-amineYield 72%

Conditions

Temperature
225 °C

Procedure

6-Chloro-2-pyridinamine (1 g, 7.78 mmol) was dissolved in morpholine (6.80 ml, 78 mmol) and heated to 225° C. in a microwave reactor for 60 minutes (˜400 W; 5 mbar). The reaction was cooled to rt and concentrated. The crude product was taken up in DCM (50 mL). After filtration of white solids the crude product was concentrated and purified by silica gel column chromatography eluting with 20-50% EtOAc/hexanes to afford 1 g (5.58 mmol, 72%) of the title compound as a pale yellow solid. LC/MS: (M+H)+: 179.9.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated
  3. filtrationAfter filtration of white solids the crude product
  4. concentrationwas concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-6de20908c8c64dcea6bc3a5bb4a85a07
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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