N,N-Diethylethylenediamine → N1,N1-Diethyl-N2-(5-phenoxy-2-pyridinyl)-1,2-ethanediamine

HRID 1448133Notes

Reaction equation

HRID 1448133 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH2:20])[CH3:16]>>[CH2:15]([N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][NH:20][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)[CH3:16]

Participants

3

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 2038206373406-95-8

Product 1

HCID 20382065N1,N1-Diethyl-N2-(5-phenoxy-2-pyridinyl)-1,2-ethanediamine

Procedure

To a solution of 3.9 g 6-chloro-3-phenoxypyridine in 5 ml n-butnaol, is added 22 g β-diethylaminoethylamine and the solution is refluxed for 72 hours. The mixture is concentrated at reduced pressure. The residue is shaken with 500 ml dichloromethane and excess dilute sodium hydroxide. The organic phase is separated, dried and distilled; bp 115°-145° C./0.1 mm. The oil is chromatographed over 150 g basic alumina (Woelm, grade I) in toluene and eluted with 0.4% MeOH in toluene. The fractions containing pure product are combined, concentrated and distilled to give 6-(β-diethylaminoethylamino)-3-phenoxypyridine; bp 143°-145° C./0.1 mm.

Workup

  1. temperaturethe solution is refluxed for 72 hours
  2. concentrationThe mixture is concentrated at reduced pressure
  3. customThe organic phase is separated
  4. customdried
  5. distillationdistilled
  6. customThe oil is chromatographed over 150 g basic alumina (Woelm, grade I) in toluene
  7. washeluted with 0.4% MeOH in toluene
  8. additionThe fractions containing pure product
  9. concentrationconcentrated
  10. distillationdistilled

Sources & evidence

ORD record
ord-32f0af23063a48a7b6d8012601d96080
Source dataset
uspto-grants-1979_12
Patent number
US04179563

Reaction notes

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