Methylamine → 6-Fluoro-N-methyl-3-pyridinemethanamine

HRID 1682212Notes

Reaction equation

HRID 1682212 reaction equation
[CH3:1][NH2:2].[F:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][CH:5]=1>CC#N>[F:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][NH:2][CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 220506385-(Bromomethyl)-2-fluoropyridine

Product 1

HCID 224503146-Fluoro-N-methyl-3-pyridinemethanamineYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2.5 g of 40% aqueous methylamine solution and 30 ml of CH3CN was added dropwise 3.0 g of crude (6-fluoro-3-pyridyl)methyl bromide with constant stirring. The mixture was allowed to stand at room temperature overnight and concentrated under reduced pressure. The residue was extracted with AcOEt and the extract was dried over MgSO4 and concentrated. The procedure gave 1.35 g of the title compound as a crude orange-colored oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue was extracted with AcOEt
  3. dry with materialthe extract was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77fe1b8c38e8428da107f260a36eefb6
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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