1,10-Decanediamine → N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate

HRID 745721Notes

Reaction equation

HRID 745721 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][CH2:17][NH2:18]>O>[OH2:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:2][P:3]([OH:6])(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 13171,10-DecanediamineHCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 86740900N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloromethanephosphonic acid (5.5 g, 42 mmoles) and 1.10-diaminodecane (44 g, 255 mmoles) were heated under reflux in water (200 cm3) for 20 hours. The water was removed and ethanol (400 cm3) added to the solid residue. The phosphonic acid was filtered off and dried. The crude yield was 11.4 g (87%). A sample was purified by recrystallization from water/ethanol to give N-(10-aminodecyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 238° C.

Workup

  1. customThe water was removed
  2. additionethanol (400 cm3) added to the solid residue
  3. filtrationThe phosphonic acid was filtered off
  4. customdried
  5. customA sample was purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-09381e4a41b946cbb8ee07e8ed0fa10d
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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