1,8-Octanediamine → N-(8-aminooctyl)-aminomethanephosphonic acid monohydrate

HRID 745723Notes

Reaction equation

HRID 745723 reaction equation
Cl[CH2:2][P:3]([OH:6])(=[O:5])[OH:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16]>O>[OH2:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:2][P:3]([OH:6])(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 242501,8-OctanediamineHCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 86740904N-(8-aminooctyl)-aminomethanephosphonic acid monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloromethanephosphonic acid (7.5 g, 58 mmoles) and 1.8-diaminooctane (50.0 g, 347 mmoles) were dissolved in water (130 cm3) and heated under reflux for 20 hours. The water was then removed and ethanol (250 cm3) added to the solid residue. The phosphonic acid was filtered off and dried. The crude yield was 13.3 g (90%). A sample was purified by recrystallization from water/ethanol to give N-(8-aminooctyl)-aminomethanephosphonic acid monohydrate as fine white solid having a melting point of 242° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customThe water was then removed
  4. additionethanol (250 cm3) added to the solid residue
  5. filtrationThe phosphonic acid was filtered off
  6. customdried
  7. customA sample was purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-f16e283ac59f45d4b147174ed4dde494
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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