GB779317A - New compounds comprising substituted piperazinediones and acid and alkali metal salts thereof, and the preparation thereof - Google Patents

New compounds comprising substituted piperazinediones and acid and alkali metal salts thereof, and the preparation thereof

Info

Publication number
GB779317A
GB779317A GB27726/55A GB2772655A GB779317A GB 779317 A GB779317 A GB 779317A GB 27726/55 A GB27726/55 A GB 27726/55A GB 2772655 A GB2772655 A GB 2772655A GB 779317 A GB779317 A GB 779317A
Authority
GB
United Kingdom
Prior art keywords
phenyl
piperazinedione
hydrogen
ethyl
racemate
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
GB27726/55A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB779317A publication Critical patent/GB779317A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises substituted piperazinediones of the formula: <FORM:0779317/IV(b)/1> in which R1 is hydrogen or a lower alkyl (1 to 6 carbon atoms), carboakloxy, carboaralkyloxy or acyl radical, R2 is hydrogen or a lower alkyl radical, R3 and R4 are hydrogen or lower alkyl radicals (one being hydrogen and one being lower alkyl) and R5 and R6 are hydrogen or phenyl (one being hydrogen and one phenyl) and acid and alkali metal salts thereof. One group of such compounds of the formula: <FORM:0779317/IV(b)/2> can be prepared by treating a -(a 1-carbethoxybenzylamino) propionitrile with a mineral acid in the presence of a lower alkyl alcohol and condensing the resulting a -(a 1-carbethoxybenzylamino) propionamide in the presence of an alkali metal lower alkoxide to obtain 3-methyl5-phenyl-piperazinedione and if desired treating this compound with a lower alkyl or acyl chloride whereby the hydrogen atoms in the N1 and N4 positions are selectively replaced by alkyl or acyl radicals, and finally if desired reacting the products with acids or bases to form salts. This group of compounds can be separated into racemic pairs of compounds, one pair being soluble in and the other pair being precipitated by hydrochloric acid. Another group of compounds, the 3-ethyl-3-phenyl-2,6-piperazinediones, may be prepared by condensing glycine ethyl ester with propiophenone and hydrogen cyanide to form a -carbethoxymethylamino-a -phenylbutyronitrile, hydrolysing with mineral acid to the corresponding carboxyamide, reacting this with methyl alcohol under esterifying conditions to give a -(carbomethoxymethylamino) - a - phenylbutyramide hydrochloride, condensation of which in the presence of sodium methoxide gives 3-ethyl-3-phenyl-2,6-piperazinedione. Other alcoholates or alkali metal amides can also be used. In examples: (1) a - (a 1 - carbethoxybenzylamino) - propionitrile hydrochloride is reacted with methanol to give a -(a 1-carbethoxybenzylamino) propionamide hydrochloride, treatment of which with sodium methoxide in ethanol gives 3-methyl-5-phenyl - 2,6 - piperazinedione; (2) and (3) the product of Example (1) dissolved in normal hydrochloric acid is treated with 12N HCl to give a precipitate consisting largely of one racemate ("Racemate B") and a filtrate containing the other racemate ("Racemate A"); (4) and (5) Racemate A and Racemate B, respectively, are reacted with carbobenzyloxy chloride to give the corresponding 4-carbobenzyloxy - 3 - methyl - 5 - phenyl - 2,6 - piperazinediones; (6) 4-carbobenzyloxy-3-methyl-5 - phenyl - 2,6 - piperizinedione is methylated in the 1-position by reaction with methyl iodide in the presence of sodium methoxide; (7) the product of (6) is decarbobenzyloxylated by treatment with hydrogen and a platinum catalyst to give 1,3-dimethyl-5-phenyl-2,6-piperazinedione hydrochloride; (8) 4-dichloroacetyl-3 - methyl - 5 - phenyl - 2,6 - piperazinedione is prepared from the product of Example (3) (Racemate B) and dichloracetyl chloride; (9) a - (carboethoxymethylamino) - a - phenylbutyronitrile hydrochloride (from the reaction of glycine ethyl ester, propiophenone and liquid hydrogen cyanide) is treated with hydrochloric acid to give a -(carboxymethylamino)-a -phenylbutyramide, which with methanol and hydrochloric acid gives a -(carbomethoxymethylamino) - a phenylbutyramide hydrochloride. This compound treated with methanol in the presence of sodium methoxide gives 3-ethyl-3-phenyl - 2,6 - piperazinedione; (10) the product of Example (9) treated with carbobenzyloxy chloride gives 4-carbobenzyloxy-3-ethyl-3-phenyl - 2,6 - piperazinedione; the product of Example (9) treated in acetic acid with formaldehyde and hydrogen in the presence of platinum oxide gives 3-ethyl-4-methyl-3-phenyl-2,6 - piperazinedione; (12) 3 - ethyl - 3 - phenyl-2,6-piperazinedione is methylated at the 1-position with methyl iodide in the presence of sodium methoxide; (13) 3-ethyl-3-phenyl-2,6-piperazinedione with phenoxyacetyl chloride gives 3 - ethyl - 4 - phenoxyacetyl - 3 - phenyl-2,6-piperazinedione. A list of other compounds corresponding to the first general formula above is given.
GB27726/55A 1954-10-08 1955-09-29 New compounds comprising substituted piperazinediones and acid and alkali metal salts thereof, and the preparation thereof Expired GB779317A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US779317XA 1954-10-08 1954-10-08

Publications (1)

Publication Number Publication Date
GB779317A true GB779317A (en) 1957-07-17

Family

ID=22140861

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27726/55A Expired GB779317A (en) 1954-10-08 1955-09-29 New compounds comprising substituted piperazinediones and acid and alkali metal salts thereof, and the preparation thereof

Country Status (1)

Country Link
GB (1) GB779317A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927114A (en) * 1958-11-14 1960-03-01 American Cyanamid Co 3, 3-disubstituted-2, 6-piperazinediones
US3194731A (en) * 1963-03-11 1965-07-13 American Cyanamid Co Method for hypnosis and tranquilization with piperazinedione derivatives
FR2178166A1 (en) * 1972-03-30 1973-11-09 Ciba Geigy Ag
FR2177916A1 (en) * 1972-03-24 1973-11-09 Ciba Geigy Ag

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927114A (en) * 1958-11-14 1960-03-01 American Cyanamid Co 3, 3-disubstituted-2, 6-piperazinediones
US3194731A (en) * 1963-03-11 1965-07-13 American Cyanamid Co Method for hypnosis and tranquilization with piperazinedione derivatives
FR2177916A1 (en) * 1972-03-24 1973-11-09 Ciba Geigy Ag
FR2178166A1 (en) * 1972-03-30 1973-11-09 Ciba Geigy Ag

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