1,3-Propanediamine → N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime

HRID 620078Notes

Reaction equation

HRID 620078 reaction equation
Cl[C:2]([CH3:8])([CH3:7])[CH:3]([N:5]=[O:6])[CH3:4].[NH2:9][CH2:10][CH2:11][CH2:12][NH2:13].[CH3:14]O>O>[NH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:2]([CH3:8])([CH3:7])[C:3](=[N:5][OH:6])[CH2:4][CH3:14]

Participants

5

Reactant 3

HCID 4281,3-PropanediamineHCID 887Methanol2×HCID 108663862-Chloro-2-methyl-3-nitrosobutane

Product 1

HCID 86585151N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-chloro-3-methyl-2-nitrosobutane (25.5 g) in methanol (180 cm3) was added dropwise to a stirred solution of 1,3-diaminopropane (47 cm3) in methanol (75 cm3) at 0° C. After the addition was complete the mixture was refluxed for 6 hours. Removal of the methanol in vacuo gave a yellow oil which was slurried in water (50 cm3). The white precipitate was removed by filtration and the pH of the aqueous solution adjusted to about 11. After saturating with salt the solution was continuously extracted with dichloromethane for 36 hours. The organic phase was dried (MgSO4) and concentrated in vacuo giving a yellow oil. Recrystallisation from ether/petrol gave pure product as a white crystalline solid, 9.9 g. Mpt. 69°-72° C.

Workup

  1. additionAfter the addition
  2. temperaturewas refluxed for 6 hours
  3. customRemoval of the methanol in vacuo
  4. customgave a yellow oil which
  5. customThe white precipitate was removed by filtration
  6. concentrationAfter saturating with salt the solution
  7. extractionwas continuously extracted with dichloromethane for 36 hours
  8. dry with materialThe organic phase was dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customgiving a yellow oil
  11. customRecrystallisation from ether/petrol
  12. customgave pure product as a white crystalline solid, 9.9 g
  13. custom69°-72° C.

Sources & evidence

ORD record
ord-f7021f16317a4c83b286041d66b8d573
Source dataset
uspto-grants-1989_04
Patent number
US04818813

Reaction notes

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