Potassium Carbonate → N-(2-Methoxybenzyl)-1-(pyridin-2-yl)methanamine

HRID 403108Notes

Reaction equation

HRID 403108 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[NH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 814952-(Chloromethyl)anisole

Product 1

HCID 791885N-(2-Methoxybenzyl)-1-(pyridin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-methoxybenzyl chloride (1.50 g, 9.5 mmol) and 2-(Aminomethyl)pyridine (5.18 g, 47 mmol) were dissolved in 800 mL CH3CN. To this solution was added potassium carbonate (1.324 g, 9.5 mmol) and the mixture was stirred at room temperature for three days. The solvent was evaporated, and the residual oil was dissolved in CH2Cl2 (75 mL) and extracted with water (75 mL×3). The combined CH2Cl2 layers were reduced in volume, and the resulting yellow-orange oil was purified by silica gel chromatography eluting with CH2Cl2, followed by a 3% (NH3)MeOH/97% CH2Cl2 solution (62%). 1H NMR (CDCl3) δ 8.520 (dd, 1H, Ar), 7.600 (m, 1H, Ar), 7.335 (d, 1H, Ar), 7.27 (d, 1H, Ar), 7.211 (t, 1H, Ar), 7.113 (m, 1H, Ar), 6.895 (t, 1H, Ar), 6.832 (d, 1H, Ar), 3.921 (s, 2H, —CH2—), 3.864 (s, 2H, —CH2—), 3.800 (s, 3H, —OCH3), 3.043 (s(br), 1H, —CH—). Mass Spec.=229.13 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residual oil was dissolved in CH2Cl2 (75 mL)
  3. extractionextracted with water (75 mL×3)
  4. customthe resulting yellow-orange oil was purified by silica gel chromatography
  5. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-411ea62c61174dc49dd3ea8cb1003752
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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