Trientine tetrahydrochloride → Triethylenetetramine

HRID 1404757Notes

Reaction equation

HRID 1404757 reaction equation
C[O-].[Na+].Cl.Cl.Cl.Cl.[NH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH2:17]>CO.C(O)C>[NH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH2:17]

Participants

5

Reactant 2

HCID 71434Trientine tetrahydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 5565TriethylenetetramineYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

In one embodiment about 4 equivalents of sodium methoxide are mixed with about 1 equivalent of triethylenetetramine tetrahydrochloride in a mixture of methanol and ethanol, for example. The reaction mixture is filtered, the solvent is evaporated, and the product is dissolved in tert-butylmethylether and again filtered and dissolved, giving triethylenetetramine in yield greater than about 95%. The triethylenetetramine is dissolved in about 2.0 equivalents of concentrated hydrochloric acid. Less than about 2 equivalents of concentrated hydrochloric acid may also be used. Ethanol is added and triethylenetetramine dihydrochloride precipitates in yield greater than about 86%. Purity of triethylenetetramine dihydrochloride so produced is about 100%, as determined using the methods set forth in USP27-NF22 (page 1890) for analysis of trientine, with less than about 10 ppm heavy metals as determined by USP <231> II.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent is evaporated
  3. dissolutionthe product is dissolved in tert-butylmethylether
  4. filtrationagain filtered
  5. dissolutiondissolved

Sources & evidence

ORD record
ord-f9ecb75b57584daea183771bd4307545
Source dataset
uspto-grants-2014_12
Patent number
US08912362B2

Reaction notes

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