Nonamethylenediamine → N-(9-aminononyl)aminomethanephosphonic acid monohydrate

HRID 745725Notes

Reaction equation

HRID 745725 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][CH2:16][NH2:17]>O>[OH2:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:2][P:3]([OH:6])(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 69534NonamethylenediamineHCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 86740906N-(9-aminononyl)aminomethanephosphonic acid monohydrateYield 157.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloromethanephosphonic acid (4.0 g, 30.6 mmoles) and 1.9-diaminononane (20.1 g, 127.2 mmoles) were dissolved in water (100 cm3) and the resultant solution heated under reflux for 20 hours. The water was then distilled off and methanol (80 cm3) added to the residue. The solid was filtered off, washed with methanol (2×50 cm3) and dried in a vacuum oven at 60° C. for three hours to yield the crude N-(9-aminononyl)aminomethanephosphonic acid monohydrate (6.5 g, 78.5%), having a melting point of 240°-241° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. distillationThe water was then distilled off
  3. additionmethanol (80 cm3) added to the residue
  4. filtrationThe solid was filtered off
  5. washwashed with methanol (2×50 cm3)
  6. customdried in a vacuum oven at 60° C. for three hours

Sources & evidence

ORD record
ord-414938b64a854fc8b39c50e68d489c7e
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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