Putrescine → N-(4-aminobutyl)-aminomethanephosphonic acid monohydrate

HRID 745724Notes

Reaction equation

HRID 745724 reaction equation
Cl[CH2:2][P:3]([OH:6])(=[O:5])[OH:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12]>O>[OH2:4].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:2][P:3]([OH:6])(=[O:5])[OH:4]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 75723P-(Chloromethyl)phosphonic acid

Product 1

HCID 86740905N-(4-aminobutyl)-aminomethanephosphonic acid monohydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloromethanephosphonic acid (7.0 g, 53.6 mmoles) and 1,4-diaminobutane (30.0 g, 340 mmoles) were heated under reflux in water (200 cm3) for 20 hours. The water was then distilled off and acetone (110 cm3) was added. The phosphonic acid was filtered off and dried. The crude yield was 9.8 g (91%). A sample was purified by recrystallization from water/ethanol to give N-(4-aminobutyl)-aminomethanephosphonic acid monohydrate as a fine white crystalline solid having a melting point of 258° C.

Workup

  1. distillationThe water was then distilled off
  2. additionacetone (110 cm3) was added
  3. filtrationThe phosphonic acid was filtered off
  4. customdried
  5. customA sample was purified by recrystallization from water/ethanol

Sources & evidence

ORD record
ord-ef5044f41d464b26979c98549f6d3906
Source dataset
uspto-grants-1986_07
Patent number
US04600429

Reaction notes

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