Morpholine → HCID 66523148, compound

HRID 594065Notes

Reaction equation

HRID 594065 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:8])[N:5]=[N:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[Cl:8][C:4]1[N:5]=[N:6][CH:7]=[C:2]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 565877855-Bromo-3-chloropyridazine

Product 1

HCID 66523148HCID 66523148, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-bromo-3-chloropyridazine (1.0 equiv.), morpholine (1 equiv.) and potassium carbonate (6 equiv.) in NMP (0.2 M) were heated to 110° C. for 4 hours in an oil bath. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over sodium sulfate, concentrated and purified by normal phase chromatography. The combined fractions were concentrated and dried under vacuo to give crude 4-(6-chloropyridazin-4-yl)morpholine and was used in the next step without further purification. LCMS (m/z) (M+H)=200.0, Rt=0.34 min.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by normal phase chromatography
  5. concentrationThe combined fractions were concentrated
  6. customdried under vacuo

Sources & evidence

ORD record
ord-3daeacffc3b74b4daa7d81a9f8748aad
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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