Dimethylamine → 1-(6-Chloropyridin-3-yl)-N,N-dimethylmethanamine

HRID 1455077Notes

Reaction equation

HRID 1455077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[CH3:10][NH:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:11]([CH3:12])[CH3:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 120566771-(6-Chloropyridin-3-yl)-N,N-dimethylmethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Chloro-5-(chloromethyl)pyridine (500 mg) was dissolved in ethanol (7.0 ml). dimethylamine (0.83 ml, 33% in ethanol) and potassium carbonate (641 mg) were added and the resulting mixture was refluxed for 1.5 hours. After evaboration of ethanol, water was added and the aqueous mixture was extracted with ethyl acetate. 1H NMR (400 MHz, d6-DMSO) δ: 8.31 (d, 1H, J 2.3 Hz), 7.77 (dd, 1H, J 8.2, 2.3 Hz), 7.47 (d, 1H, J 8.2 Hz), 3.41 (s, 2H), 2.14 (s, 6H).

Workup

  1. temperaturethe resulting mixture was refluxed for 1.5 hours
  2. extractionthe aqueous mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-a72f5db53d9240e08e12fcd5aba29a27
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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