Methylamine → N-Methylpyridine-4-methylamine

HRID 1387611Notes

Reaction equation

HRID 1387611 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][CH:3]=1.[CH3:10][NH2:11]>O>[CH3:10][NH:11][CH2:8][C:5]1[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 81436N-Methylpyridine-4-methylamineYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-picolyl chloride, hydrochloride (10 g, 0.06 mol) was added methylamine (50 mL of 40% aqueous solution, 0.58 mol), and the resulting purple solution was stirred at rt for 30 min, then poured into H2O. The mixture was extracted with CH2Cl2 (6×), and the combined organic extracts were evaporated. The residue was filtered under reduced pressure through a silica gel column, eluting with a solvent gradient of 0-10% MeOH/CHCl3 to provide the title compound as a light yellow oil (4.8 g, 66%): 1H NMR (CDCl3): d 8.50 (dd, 2H); 7.20 (dd, 2H); 3.70 (s, 2H); 2.40 (s, 3H); 1.70 (br, 1H).

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (6×)
  2. customthe combined organic extracts were evaporated
  3. filtrationThe residue was filtered under reduced pressure through a silica gel column
  4. washeluting with a solvent gradient of 0-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-1f530dedc7c8419a95c865abc1d868b0
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

Loading…