2-Aminopropanol → 1-Methyl-2-(4-pyridyloxy)ethylamine

HRID 1900168

Reaction equation

HRID 1900168 reaction equation
[NH2:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].Cl.Cl[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH3:5][CH:2]([NH2:1])[CH2:3][O:4][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 51262-AminopropanolHCID 24758Sodium hydrideHCID 818524-Chloropyridine hydrochloride

Product 1

HCID 544990201-Methyl-2-(4-pyridyloxy)ethylamineYield 30.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 mL of N,N-dimethylformamide at 5° C.-10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stirred for 20 hours at room temperature. After completion of the reaction, the solids were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 3.8 g of the desired product (yield: 30%). Refractive index: 1.5469.

Workup

  1. stirringThe mixture was stirred for 20 hours at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe solids were filtered off
  4. customThe solvent in the filtrate was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-64e63c4358cb4c6fbafa06e0eafb27bc
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Linked notes

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