Sodium Methoxide → HCID 66783704, compound

HRID 1096838Notes

Reaction equation

HRID 1096838 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([CH2:9][NH:10][CH:11]2[CH2:13][CH2:12]2)[CH:5]=[CH:4][N:3]=1.[CH3:14][O-:15].[Na+]>O1CCOCC1>[CH:11]1([NH:10][CH2:9][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:15][CH3:14])[C:7]=2[CH3:8])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86008531HCID 86008531, compound

Product 1

HCID 66783704HCID 66783704, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2-chloro-3-methylpyridin-4-ylmethyl)cyclopropylamine (10.0 g, 50.8 mmol) and sodium methoxide (13.73 g, 254 mmol) in dioxan (40 mL) was heated to reflux for 48 h. The reaction mixture was filtered through Celite, and the remaining solid was washed with Et2O (2×). The solvents were removed under reduced pressure. Purification by FC yielded the title compound (8.8 g, 90%) as a pale, yellow liquid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe remaining solid was washed with Et2O (2×)
  5. customThe solvents were removed under reduced pressure
  6. customPurification by FC

Sources & evidence

ORD record
ord-c67e8435e9e24c77b219d46fb9f608c3
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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