Sodium Azide → HCID 21432767, compound

HRID 2399122Notes

Reaction equation

HRID 2399122 reaction equation
Cl.Cl[CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C)C=O>[N:13]([CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21432754HCID 21432754, compound

Product 1

HCID 21432767HCID 21432767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of 2-(2-chloroethoxymethyl)pyridine hydrochloride and sodium azide (9.8 g.) in dry dimethylformamide (103 ml.) is maintained at 95° for 5 hours and then set aside overnight at room temperature. Following dilution with water and filtration, the filtrate is concentrated and the residue purified by chromatography on a dry column of alumina using ethanol. The product is basified with potassium carbonate (6.5 g.) in water (3 ml.) and the anhydrous residue is extracted with isopropyl alcohol (3 × 50 ml.). Concentration of the extracts gives 2-(2-azidoethoxymethyl)pyridine. Hydrogenation of the azido compound in isopropyl alcohol over platinum oxide catalyst gives 2-(2-aminoethoxymethyl)pyridine.

Workup

  1. temperatureis maintained at 95° for 5 hours
  2. filtrationwith water and filtration
  3. concentrationthe filtrate is concentrated
  4. customthe residue purified by chromatography on a dry column of alumina
  5. extractionthe anhydrous residue is extracted with isopropyl alcohol (3 × 50 ml.)

Sources & evidence

ORD record
ord-455a29c90b9e4f3eb33fb3ba05fd65e3
Source dataset
uspto-grants-1977_05
Patent number
US04027026

Reaction notes

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