Sodium Hydroxide → 2-(2-Dimethylaminoethylamino)-6-dimethylaminomethylpyridine

HRID 1395532Notes

Reaction equation

HRID 1395532 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]([CH3:11])[CH3:10])[N:3]=1.[CH3:12][N:13]([CH2:15][CH2:16][NH2:17])[CH3:14].[OH-].[Na+]>N1C=CC=CC=1>[CH3:12][N:13]([CH3:14])[CH2:15][CH2:16][NH:17][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]([CH3:11])[CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66053N,N-DimethylethylenediamineHCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

Product 1

HCID 203395272-(2-Dimethylaminoethylamino)-6-dimethylaminomethylpyridineYield 35.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloro-6-dimethylaminomethylpyridine (14 g., 0.0825 mole) and unsym-dimethylethylenediamine (21.8 g, 0.248 mole) in 10 ml of pyridine are heated at 180° for 8 hours in a bomb. The dark reaction mixture is stirred over 20 g of solid sodium hydroxide for 1 hour on a steam bath. Then the mixture is filtered. Distillation of the filtrate gives 6.5 g of product, b.p. 110°-11° at 0.1 mm, nD25 1.5287.

Workup

  1. customThe dark reaction mixture
  2. filtrationThen the mixture is filtered
  3. distillationDistillation of the filtrate

Sources & evidence

ORD record
ord-2118240aacf4412685a1411ec7e1eef5
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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