Hexamethylenediamine → N-(6-aminohexyl)-aminomethanephosphonic acid monohydrate

HRID 745720Notes

Reaction equation

HRID 745720 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][NH2:14]>O>[OH2:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:2][P:3]([OH:6])(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 16402HexamethylenediamineHCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 86740899N-(6-aminohexyl)-aminomethanephosphonic acid monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloromethanephosphonic acid (6.5 g, 49.8 mmoles) and 1.6-diaminohexane (34.8 g, 300 mmoles) were dissolved in water (130 cm3) and heated under reflux for 20 hours. The water was removed and ethanol (250 cm3) was added to the solid residue. The phosphonic acid was filtered off and dried. The crude yield was 10.4 g (92%). A sample was purified by recrystallization from water/ethanol to give N-(6-aminohexyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 235° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customThe water was removed
  4. additionethanol (250 cm3) was 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-1f74a984e1044d61a0a328a35fa3b720
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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