Morpholine → 2-Methyl-4-chloro-6-morpholino-pyridine

HRID 252983Notes

Reaction equation

HRID 252983 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 119590832,4-Dichloro-6-methylpyridine

Product 1

HCID 575505222-Methyl-4-chloro-6-morpholino-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-Methyl-4,6-dichloropyridine (256 mmol) is dissolved in dichloromethane (200 mL) and chilled to −78° C. in an inert atmosphere. Morpholine (550 mol) dissolved in dichloromethane (100 mL) is added slowly. The reaction is allowed to warm to room temperature while stirring overnight. The organic layer is washed with saturated ammonium chloride (2×100 mL), dried with sodium sulfate, and evaporated to give 2-methyl-4-chloro-6-morpholino-pyridine.

Workup

  1. additionis added slowly
  2. temperatureto warm to room temperature
  3. washThe organic layer is washed with saturated ammonium chloride (2×100 mL)
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f6527866ffd046748a51042fcc0e358d
Source dataset
uspto-grants-2011_01
Patent number
US07872005B2

Reaction notes

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