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

HRID 249498Notes

Reaction equation

HRID 249498 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-ff7303e61a52457e822613e7b2d9a235
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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