GB754873A - Dicarnitine dichloride and a process for the preparation thereof - Google Patents

Dicarnitine dichloride and a process for the preparation thereof

Info

Publication number
GB754873A
GB754873A GB13450/54A GB1345054A GB754873A GB 754873 A GB754873 A GB 754873A GB 13450/54 A GB13450/54 A GB 13450/54A GB 1345054 A GB1345054 A GB 1345054A GB 754873 A GB754873 A GB 754873A
Authority
GB
United Kingdom
Prior art keywords
dichloride
dicarnitine
solution
agent
vacuo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB13450/54A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Labaz Sanofi NV
Original Assignee
Labaz Laboratoires SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Labaz Laboratoires SA filed Critical Labaz Laboratoires SA
Publication of GB754873A publication Critical patent/GB754873A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/02Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/22Separation; Purification; Stabilisation; Use of additives
    • C07C231/24Separation; Purification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises the b -hydroxy-g -trimethylammonium chloride butyrate of b -hydroxy-g -trimethylammonium chloride butyric acid (dicarnitine dichloride) of the formula <FORM:0754873/IV(a)/1> and a process for the preparation thereof by dissolving b -hydroxy-g -trimethylammoniumchloridebutyronitrile in concentrated hydrochloric acid, e.g. with approximately twice its weight of concentrated hydrochloric acid, and heating the resulting solution under pressure, e.g. at a temperature between 100 DEG and 140 DEG C. for several hours. The desired product may be isolated from the reaction product after removing ammonium chloride by fractional crystallization, or insoluble ammonium chloride may be separated from the dicarnitine dichloride solution by cooling and a first fraction of the dichloride is recovered from the acid solution by concentrating the solution in vacuo, the resulting crystals are treated with a mixture of hydrophilic solvents one of which is a solubilizing agent and the other a precipitating agent for the dichloride and the mother liquor is separated from the undissolved dicarnitine dichloride, or the mother liquid obtained after recovering the first fraction of the dichloride referred to above may be evaporated in vacuo, the residue taken up in concentrated hydrochloric acid, purified by means of activated charcoal in an aqueous medium and evaporated in vacuo, the crystals thus obtained are then treated with a mixture of the hydrophilic solvents as above to form a second fraction of dicarnitine dichloride. Anhydrous methanol may be used as the solubilizing agent and anhydrous acetone as the precipitating agent for the mixture of hydrophilic solvents. The ratio by volume of solibilizing agent to precipitating agent is preferably lower than 1 in 5-particularly in the neighbourhood of 1 in 10. An alternative method given for the preparation of dicarnitine dichloride is by reacting g -chloro-b -hydroxybutyronitrile and trimethylamine under pressure in alcoholic solution to form g -trimethylammoniumchloride-b -hydroxybutyrocyanide which is then treated as above. A detailed example is given.
GB13450/54A 1953-05-08 1954-03-07 Dicarnitine dichloride and a process for the preparation thereof Expired GB754873A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE754873X 1953-05-08

Publications (1)

Publication Number Publication Date
GB754873A true GB754873A (en) 1956-08-15

Family

ID=3879726

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13450/54A Expired GB754873A (en) 1953-05-08 1954-03-07 Dicarnitine dichloride and a process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB754873A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT382365B (en) * 1984-03-28 1987-02-25 Chemiosyntex Srl METHOD FOR PRODUCING THE NEW ACETYLDICARNITINE DICHLORIDE
US4743621A (en) * 1984-07-04 1988-05-10 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Ester of acetyl carnitine, processes for its preparation and pharmaceutical compositions containing it

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT382365B (en) * 1984-03-28 1987-02-25 Chemiosyntex Srl METHOD FOR PRODUCING THE NEW ACETYLDICARNITINE DICHLORIDE
US4743621A (en) * 1984-07-04 1988-05-10 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Ester of acetyl carnitine, processes for its preparation and pharmaceutical compositions containing it

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