DE2355257A1 - 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide - Google Patents

2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide

Info

Publication number
DE2355257A1
DE2355257A1 DE19732355257 DE2355257A DE2355257A1 DE 2355257 A1 DE2355257 A1 DE 2355257A1 DE 19732355257 DE19732355257 DE 19732355257 DE 2355257 A DE2355257 A DE 2355257A DE 2355257 A1 DE2355257 A1 DE 2355257A1
Authority
DE
Germany
Prior art keywords
tricyclohexyl
trimethyl
phosphoric acid
dibromo
amino
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.)
Pending
Application number
DE19732355257
Other languages
German (de)
Inventor
Johannes Dipl Chem Dr Keck
Gerd Dipl Chem Dr Krueger
Helmut Dipl Chem Dr Pieper
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
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 Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Priority to DE19732355257 priority Critical patent/DE2355257A1/en
Publication of DE2355257A1 publication Critical patent/DE2355257A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/224—Phosphorus triamides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Abstract

(A) The following process is new: Physiologically-acceptable acid addition salts of (I) with inorganic or organic acids are included. (B) N,N',N"-tricyclohexyl-N,N'.N-trimethyl-phosphoric acid triamide (III) is a novel cpd.

Description

Case 5/596 I
Dr.Pl./Kp.Case 5/596 I.
Dr.Pl./Kp.

DR. KARL THOMAS GMBH.,BIBERACH AN DER RISSDR. KARL THOMAS GMBH., BIBERACH AN DER RISS

N4N1 ,N"-Tricyclohexyl-N4N' ,Ν''-trimethyr-phosphorsäure-N 4 N 1 , N "-Tricyclohexyl-N 4 N ', Ν" - trimethyr-phosphoric acid-

triamid yi^^^cA \j*Λ<Λ-«Λ^-* ■ Qr-v Ο^λ-λγ Ku'Vw^/s-ytriamid yi ^^^ cA \ j * Λ <Λ- « Λ ^ - * ■ Qr-v Ο ^ λ-λγ Ku'Vw ^ / sy

(Ausscheidung aus der Patentanmeldung P 23 37 931.9) ^ (Separation from patent application P 23 37 931.9) ^

Gegenstand der vorliegenden Anmeldung ist die neue Verbindung N,N',N"-TricycXohexyl-N,N',N"-trimethyi-phösphorsäure-triamid und ein Verfahren zu ihrer Herstellung.The subject of the present application is the new compound N, N ', N "-TricycXohexyl-N, N', N" -trimethylphosphoric acid triamide and a method for their production.

Die oben bezeichnete Verbindung ist ein wertvolles neues ,Zwischenprodukt zur Herstellung von pharmazeutisch wertvollen !Verbindungen, insbesondere zur Herstellung von 2-Amino-N-cyclo~ hexyl-345-dibrom-N^methyl-benzylamin.The compound named above is a valuable new intermediate product for the preparation of pharmaceutically valuable compounds, in particular for the preparation of 2-amino-N-cyclo-hexyl-3 4 5-dibromo-N-methyl-benzylamine.

iDie neue Ausgangsverbindung läßt sich nach folgendem Verfahren ■herstellen: ; iThe new starting compound can be prepared by the following method ■:;

Umsetzung eines Phosphoroxyhalogenids mit N-Methyl-cyclohexylamin, gegebenenfalls in Gegenwart einer tertiären organischen Base. . .Reaction of a phosphorus oxyhalide with N-methyl-cyclohexylamine, optionally in the presence of a tertiary organic Base. . .

Das nachfolgende Beispiel soll die Erfindung näher erläutern:The following example is intended to explain the invention in more detail:

5098 18/11435098 18/1143

Beispiel 1example 1 NyN' ^"-Tricyclohexyl-NsN1,N"-trimethyl-phosphorsäuretriamidNyN '^ "- Tricyclohexyl-NsN 1 , N" -trimethyl-phosphoric acid triamide

306 g N-Methyl-cyclohexylamin werden unter Rühren während 20 Minuteri mit 46 g Phosphoroxychlorid versetzt und dann 3 Stunden unter Rückfluß gekocht (ölbad, 1700C). Anschließend wird die abgekühlte Reaktionslösung in 1,2 1 Chloroform und 0,8 1 Wasser aufgenommen, die organische Phase noch zweimal mit Wasser, zweimal mit 2n Essigsäure und einmal mit 2n Ammoniak ausgeschüttelt, mit Natriumsulfat getrocknet und eingeengt. Der Rückstand wird über eine Kieselgelsäule mit Chloroform-Essigester (1:1) chromatographiert. Die entsprechenden Fraktionen werden vereinigt, eingeengt und der Rückstand in Petroläther aufgenommen, wonach eine geringe Menge eines Nebenprodukts kristallisiert, das nach längerem Stehen abgesaugt wird. Das Piltrat engt man zur Trockene ein, am Schluß bei 100°C und 15 Torr. Das als öl erhaltene N,N1,N"-Tricyclohexyl-N,N1 ,Ν''-trimethyl-phosphorsäuretriamid kristallisiert langsam durch,
ßchmelzpunkt: 60 -306 g N-methyl-cyclohexylamine are added, with stirring for 20 Minuteri with 46 g of phosphorus oxychloride and then boiled for 3 hours under reflux (oil bath, 170 0 C). The cooled reaction solution is then taken up in 1.2 l of chloroform and 0.8 l of water, the organic phase is extracted twice more with water, twice with 2N acetic acid and once with 2N ammonia, dried with sodium sulfate and concentrated. The residue is chromatographed on a silica gel column with chloroform-ethyl acetate (1: 1). The appropriate fractions are combined and concentrated, and the residue is taken up in petroleum ether, after which a small amount of a by-product crystallizes, which is filtered off with suction after standing for a long time. The Piltrat is concentrated to dryness, at the end at 100 ° C and 15 Torr. The N, N 1 , N "-Tricyclohexyl-N, N 1 , Ν" - trimethyl-phosphoric acid triamide obtained as an oil slowly crystallizes through,
Melting point: 60 -

'509818/1143'509818/1143

Claims (2)

F at ent ans ρ r ü ehe .F at ent ans ρ r ü ehe. 1. N , N', N " -Tri cy c lohexy 1-N, N', N " -1 rime thy l-phö sphors gure--1 r i ami d.1. N , N ', N "-Tri cy c lohexy 1-N, N', N" -1 rime thy l-phö sphors gure - 1 ri ami d. 2. Verfahren zur Herstellung der Verbindung gemäß Anspruch 1, dadurch gekennzeichnet,daß ein Phosphorpxytrihalogenid mit N-Methyl-N-'cyclohexylamin umgesetzt wird.2. Process for the preparation of the compound according to claim 1, characterized in that a Phosphorpxytrihalogenid with N-methyl-N-'cyclohexylamine is implemented.
DE19732355257 1973-07-26 1973-07-26 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide Pending DE2355257A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19732355257 DE2355257A1 (en) 1973-07-26 1973-07-26 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19732355257 DE2355257A1 (en) 1973-07-26 1973-07-26 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide

Publications (1)

Publication Number Publication Date
DE2355257A1 true DE2355257A1 (en) 1975-04-30

Family

ID=5897259

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19732355257 Pending DE2355257A1 (en) 1973-07-26 1973-07-26 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N',N''-tricyclohexyl-N,N',N''-trimethyl-phosphoric acid triamide

Country Status (1)

Country Link
DE (1) DE2355257A1 (en)

Similar Documents

Publication Publication Date Title
DE1644306B2 (en) BASIC ANTHRAQUINONE AND NITRODINES AND PROCESS FOR THEIR PRODUCTION
EP0609179B1 (en) Preparation of aromatic nitriles
DE60004126T2 (en) Process for the preparation of (1R, 2S, 4R) - (-) - 2 - [(2 &#39;- (N, N-dimethylamino) ethoxy)] - 2- [phenyl] -1,7,7-tri- [ methyl] bicyclo [2.2.1] heptane and its pharmaceutically acceptable acid addition salts
DE2010182A1 (en) New process for the production of cis-chrysanthemum acids
DE2355257A1 (en) 2-Amino-N-cyclohexyl-3,5-dibromo-N-methylbenzyl-amine prepn - by reacting benzylalcohol with N,N&#39;,N&#39;&#39;-tricyclohexyl-N,N&#39;,N&#39;&#39;-trimethyl-phosphoric acid triamide
EP1476446B1 (en) Method for producing n-ethyl-n-( 3-(3-cyanopyrazolo-(1,5a)-pyrimidine-7-yl)phenyl)-acetamide
DE1793693C3 (en)
DE2011078C3 (en) Process for purifying hexetidine
EP0104566B1 (en) Process for the preparation of 5,11-dihydro-11-((4-methyl-1-piperazinyl)-acetyl)-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one
DE1932402B2 (en) Isopropyl-4-phenyl-3,4-dihydro-2 (1H) quinazolinone derivatives and their further processing to 1-isopropyl-4-phenyl-2 (1H) quinazolinones
AT332427B (en) PROCESS FOR PRODUCING THE NEW N, N &#39;, N &#34;- TRICYCLOHEXYL -N, N&#39;, N&#34; - TRIMETHYL -PHOSPHORIC ACID TRIAMIDE
DE2112778A1 (en) Process for the preparation of 2-cyano-3,4,5,6-tetrahalogenobenzoic acid alkyl esters
EP0065200B1 (en) Thiolactime ethers of delta-1-pyrrolidine, and their preparation
DE2816627A1 (en) Antihypertensive isoindolinyl-amino-imidazoline - prepd. by reacting 2-amino-isoindoline with 2-alkylthio-2-imidazoline
DE2354327B2 (en) 2-AMINO-1,2,3,4-TETRAHYDRONAPHTHALINE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND PROCESSES FOR THE PREPARATION OF 6,7-BENZOMORPHANS STARTING FROM THEM
FI61311C (en) NYTT FOERFARANDE FOER FRAMSTAELLNING AV 2-ACYLAMINO-BENTSYLAMINER
DE2150267C3 (en) Process for the production of peptides
EP0110202A2 (en) Process for the preparation of phenylethanol amines
DE3209789C2 (en) Process for the preparation of 1- (3-hydroxyphenyl) -2-nitropropen- (1)
AT337173B (en) PROCESS FOR THE PRODUCTION OF NEW ISOINDOLINE DERIVATIVES AND THEIR SALT
DE1470379C (en) 11 (1 methyl 4 piperidyhden) morphan thridin its acid salts and manufacturing process
DE2116314A1 (en) Method of making L-dopa
DE2819798A1 (en) PROCESS FOR PRODUCING 3-PHENYL-PYRIDAZONE- (6)
EP0015882A1 (en) Undecanoic acids and esters thereof, and a process for their preparation
DE2214518A1 (en) New process for the production of cyclic ureas

Legal Events

Date Code Title Description
OHJ Non-payment of the annual fee