Morpholine → 4-(6-Chloropyridazin-3-yl)morpholine

HRID 416235Notes

Reaction equation

HRID 416235 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1>>[Cl:7][C:8]1[N:9]=[N:10][C:11]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 673313,6-Dichloropyridazine

Product 1

HCID 3210794-(6-Chloropyridazin-3-yl)morpholineYield 79.1%

Conditions

Temperature
90 °C

Procedure

A 50 mL flask equipped with a reflux condenser was charged with morpholine (2.93 mL, 33.5 mmol) and 3,6-dichloropyridazine (5.00 g, 33.5 mmol). The mixture was heated at 90° C. for 6 h, the resultant solid was partitioned between EtOAc, water and saturated NH4Cl. Organic layer was separated, dried over anhydrous Na2SO4, filtered, and evaporated to afford the title compound 64 (5.3 g, 26.5 mmol, 79% yield).

Workup

  1. customA 50 mL flask equipped with a reflux condenser
  2. customthe resultant solid was partitioned between EtOAc, water and saturated NH4Cl
  3. customOrganic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-347ec66b98f74d89a732af63a249016c
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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