N-3-Bromopropylphthalimide → Diethyl (3-aminopropyl)phosphonate

HRID 1886312Notes

Reaction equation

HRID 1886312 reaction equation
BrCCC[N:5]1[C:9](=O)[C:8]2=[CH:11]C=CC=C2C1=O.[P:16]([O:23]CC)([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>>[NH2:5][CH2:9][CH2:8][CH2:11][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 21611N-3-BromopropylphthalimideHCID 31215Triethyl phosphite

Product 1

HCID 78113Diethyl (3-aminopropyl)phosphonateYield 34%

Conditions

Temperature
140 °C

Procedure

70 ml of triethyl phosphite was added to 40 g of N-(3-bromopropyl)phthalimide (7). The mixture was heated to a temperature of 140° C. The by-produced ethyl bromide was distilled off. The system was then heated over 4 hours. Excess triethyl phosphite was distilled off under reduced pressure by an aspirator. 9 ml of ethanol and hydrazine hydrate were added to the concentrated solution. The system was heated under reflux over 20 minutes. The resulting crystals were filtered off. A mixture of 10 g of oxalic acid and 50 ml of acetone were added to the filtrate. The resulting crystals were filtered off. The filtrate was concentrated. A small amount of water and acetone were added to the residue. The resulting crystals were filtered off. The filtrate was cooled to deposit crystals of oxalic acid salt of diethyl 3-aminopropylphosphonate (8). The crystals were filtered and dried under reduced pressure by a vacuum pump to obtain 12 g of diethyl 3-aminopropylphosphonate (8) in the form of oxalate. (Yield: 34 %; m.p. 54° C.)

Workup

  1. distillationThe by-produced ethyl bromide was distilled off
  2. temperatureThe system was then heated over 4 hours
  3. distillationExcess triethyl phosphite was distilled off under reduced pressure by an aspirator
  4. addition9 ml of ethanol and hydrazine hydrate were added to the concentrated solution
  5. temperatureThe system was heated
  6. temperatureunder reflux over 20 minutes
  7. filtrationThe resulting crystals were filtered off
  8. additionA mixture of 10 g of oxalic acid and 50 ml of acetone
  9. additionwere added to the filtrate
  10. filtrationThe resulting crystals were filtered off
  11. concentrationThe filtrate was concentrated
  12. additionA small amount of water and acetone were added to the residue
  13. filtrationThe resulting crystals were filtered off
  14. temperatureThe filtrate was cooled
  15. filtrationThe crystals were filtered
  16. customdried under reduced pressure by a vacuum pump

Sources & evidence

ORD record
ord-bed04043f5d34444afa66858ea0176b8
Source dataset
uspto-grants-1992_09
Patent number
US05151357

Reaction notes

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