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

HRID 927

Reaction equation

HRID 927 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-6d97a1bfa8604b93849d4516305a87c9
Source dataset
uspto-grants-1998_03
Patent number
US05723469

Linked notes

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