1,8-Octanediamine → HCID 86740901, compound

HRID 745722Notes

Reaction equation

HRID 745722 reaction equation
C(C[C:4]([CH2:10]C)(Br)[P:5]([O-:8])(=[O:7])[O-:6])C.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH2:21]>O>[OH2:6].[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:10][CH2:4][P:5]([OH:6])(=[O:7])[OH:8]

Participants

4

Reactant 2

HCID 242501,8-OctanediamineHCID 86740902HCID 86740902, compound

Product 1

HCID 86740901HCID 86740901, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethylbromoethanephosphonate (15.3 g, 0.062 moles) and 1.8-diaminooctane (54.0 g, 0.375 moles) were heated under reflux in water (250 cm3) for 5 hours. The water and excess diamine were then distilled off. Concentrated hydrochloric acid (280 cm3) was added and the solution heated under reflux for 8 hours. The solution was then evaporated to dryness on a rotary evaporator and the residue was dissolved in methanol (75 cm3) and propylene oxide wad added to pH 6. The phosphonic acid was filtered off and dried. The crude yield was 10.2 g (60.5%). A sample was purified by recrystallization from water/ethanol to give N-(8-aminooctyl)-2-aminoethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 210° C.

Workup

  1. distillationThe water and excess diamine were then distilled off
  2. additionConcentrated hydrochloric acid (280 cm3) was added
  3. temperaturethe solution heated
  4. temperatureunder reflux for 8 hours
  5. customThe solution was then evaporated to dryness on a rotary evaporator
  6. dissolutionthe residue was dissolved in methanol (75 cm3)
  7. additionpropylene oxide wad added to pH 6
  8. filtrationThe phosphonic acid was filtered off
  9. customdried
  10. customA sample was purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-4cc70b3b9a504126baf7d134cd47deda
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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