DE1967049A1 - Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen - Google Patents

Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

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Publication number
DE1967049A1
DE1967049A1 DE19691967049 DE1967049A DE1967049A1 DE 1967049 A1 DE1967049 A1 DE 1967049A1 DE 19691967049 DE19691967049 DE 19691967049 DE 1967049 A DE1967049 A DE 1967049A DE 1967049 A1 DE1967049 A1 DE 1967049A1
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Prior art keywords
pyridyl
tetrahydropyran
tetrahydropyrans
preparation
alkali metal
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.)
Withdrawn
Application number
DE19691967049
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English (en)
Inventor
Roy Dennis Bowden
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Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of DE1967049A1 publication Critical patent/DE1967049A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/51—Acetal radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

Flappe 23929 - Dr. K/by
IGI Case HD 22902 C
IHPERIAL CHEMICAL INDUSTRIES LTD.
London, Großbritannien
"Verfahren zur Herstellung von 4-(Pyridyl)-tetrahydropyranen"
Die Erfindung bezieht sich, auf Pyridinderivate und deren Herstellung und insbesondere auf neue substituierte Pyridine sowie auf ein Verfahren zur Herstellung von substituierten 'Pjridinen. , ;
Gemäß der Erfindung werden als. neue Verbindungen 4-(Pyridyl)-tetrahydropyrane vorgeschlagen. Die. Tetrahydropyranylgruppe
kann an das. Kohlenstoffatom in der 2-, 3- oder 4--S te llung
des Pyridinkerns gebunden sein.
609845/0993
Unsubstituierte 4-(Pyridyl tetrahydropyrane besitzen die folgende allgemeine Strukturformel:
In den Bereich der Erfindung fallen auch Verbindungen, die diese Grundformel aufweisen, aber ein oder mehrere Substituenten enthalten, wie z.B. Alkyl- oder Alkoxy gruppen im Pyridylkern und/oder Tetrahydropyranylkern.
4—(Pyridyl)tetrahydropyrane können dadurch hergestellt werden, daß man einen 2l-Halogenäthyl-3-(pyridyl)propyläther mit einer aktiven Alkalimetallverbindung umsetzt. Die Reaktionsteilnehmer werden vorzugsweise in äquimolaren Mengen und vorzugsweise bei einer Temperatur im Bereich von -10 bis -800C in Lösung in einem flüssigen Ammoniak enthaltenden Medium umgesetzt. Jedoch kann die Reaktion in Abwesenheit eines Lösungsmittels oder in anderen Lösungsmitteln als flüssigem Ammoniak ausgeführt werden, beispielsweise in Kohlenwasserstoffen und Äthern, in welchen Fällen höhere Temperatüren, beispielsweise bis zu 4-00C, verwendet werden können. Höhere Temperaturen können auch dadurch erreicht werden, daß man die Reaktion unter überatmosphärischem Druck ausführt. Die bevorzugten aktiven Alkalimetallverbindungen sind Alkalimetallamide, insbesondere Natriumamid.
Das 4—(Pyridyl)tetrahydropyran kann aus dem Reaktionsgemisch durch herkömmliche Techniken isoliert werden, beispielsweise dadurch, daß man den Metallamidüberschuß durch Zusatz eines Ammoniumsalzes zerstört, das resultierende-Produkt mit einem organischen Lösungsmittel, das bei gewöhnlichen Temperaturen flüssig ist, wie z.B. Äther, extrahiert, die organische Schicht mit Wasser wäscht und das organische Lösungsmittel und das Produkt durch Destillation trennt.
_ 2 ■■--■'-■ ■. ■' -
Die durch das erfindungs gemäße Terfahren lierge st ell tea 4-(Pyridyl)tetrahydropyrane können in .-
das entsprechende Bipyridyl durch Umsetzung mit Ammoniak in der Dampfphase überführt werden. Die Seaktion wird vorzugsweise in Gegenwart von molekularem Sauerstoff ausgeführt.
Die Erfindung wird durch das folgende Beispiel näher erläutert: . -.■,.■■"■■--".·.".-,.■■ .-■"._ .0.."; :; ....'.."■' -
BEISPIEL· -/ .'■"":"-;■
Zu 1 1 gerührtem flüssigem Ammoniak wurden 0,1 g Eis en (III)-nitrat und dann 20,0 g Kaliummetall in 1 g wiegenden Stücken während eines Zeitraums von 30 min zugegeben. Zur resultierenden Losung wurden 46,6 g gammä-Picolinτwährend eines Zeitraums von 3 min zugesetzt, worauf sich eine tiefgelbe Farbe entwickelte. -
Die Losung wurde zu einer gerührten Lösung von 72,0 g 2,2'-DiCchloroäthyl)äther in Λ 1 flüssigem Ammoniak mit einer solchen Geschwindigkeit (gesamte Zugabezeit 20 min) zugegeben, daß keine gelbe Farbe bestehen blieb. Diese Lo&ung wurde mit "Lösung A" bezeichnet.
Zu Λ 1 gerührtem flüssigem Ammoniak wurden 0,1 g Eisen(III)-nitrat und dann 20,0 g Zaliummetall in Igwiegenden Stücken während eines Zeitraums von 30min zugegeben. Die resultierende Lösung wurde 20 min gerührt und zur Lösung A mit einer solchen Geschwindigkeit zugegeben, daß sich nur eine blaßgelbe Farbe entwickelte. Das Gemisch wurde 1 st- gerühmt, und dann wurden 20 g Ammoniumchlorid langsam zugesetzt, worauf noch 1 1 Äther zugegeben wurde» Das GemischI wurde auf Raumtemperatur erwärmen gelassen, filtriert und mit Wasser gewaschen. Das Lösungsmittel wurde entfernt, und der Rückstand wurde destilliert4 wobei 30 g 4-(4l-i^ridyl)tetrahydroKrran mit den folgenden Eigenschaften erhalten wurden:
Siedepunkt 1-15-118°C/1 mm Hg
Schmelzpunkt 60-62°C
Infrarot V max (flüssiger Film) 3070, 3025, 2940, 2845,
1600, 1410, 1130, 1085, 990 und 900 cm""1 NMR C (CDCl3) 1,5, 2,85, 5,9, 6,5, 7,25, 8,25
(relative Intensitäten 2:2:2:2:1:4)
Massenspektrum: γ = 163,0998 (C10H15ITO hat j = 163,0997) 132,130, 119, 105, 92 und 78
Eine höher siedende Fraktion (5 g) wurde ebenfalls gesammelt und als Bl-3-(W -pyridyl)prop-1-yläther mit einem Kp von 2150C/ 1 mm Hg identifiziert.
In ähnlicher Weise wurde aus alpha-Picolin 4-(2'-Pyridyl)— tetrahydropyran erhalten, das durch die folgenden Spektral— daten identifiziert wurde: '
Massenspektrum: β = 163 (C10H15ITO hat j = 163)
In ähnlicher Weise wurde aus beta-Picolin 4-(3·-Pyridyl)tetrahydropyran mit einem Fp von 34-00C erhalten, das durch die folgenden Spektraldaten identifiziert wurde:
Infrarot ν max (CCl4) 2950, 2850, 1460, 1440, 1430, 1375, 1120, 1090, 1020 und 900 cm"1
ITMRz; (CCl4) 1,5, 2,5, 2,8, 5,95, 6,5, ,7,2 und 8,25 (relative Intensitäten 2:1:1:2:2:1:4)
Massenspektrum: j = 163,1004 (C10H15NO hat Jf » 163,0997)
_ 4 ■ 6098 4570993

Claims (8)

  1. PATEITTAIf SPRÜCHE: : . -" =:'
    \1y Verfahren zur Herstellung eines, 4-(Pyridyl)tetrahydropyrans, dadurch gekerinzeichnet, daß man einen 2'-Halogenäthyl-3-(pyridyl)propyläther mit einer aktiven Alkalimetallverbindung umsetzt.
  2. 2. Verfahren nach Anspruch1, dadurch gekennzeichnet, daß die Reaktion bei einer Temperatur bis zu 400C ausgeführt wird. ■""-.".. "."--....."-.
  3. 3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß eine Temperatur von -80 bis -1O0G verwendet wird,
  4. 4. Verfahren nach Anspruch T1. 2 oder 3» dadurch gekennzeichnet, daß die Reaktion in.flüssigem Ammoniak ausgeführt wird. "
  5. 5. Verfahren nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß als aktive Alkalimetallverbindung ein AlkalimetaHamid verwendet wird. . :
  6. 6. Verfahren nach Anspruch 5i dadurch gekennzeichnet, daß Hatriumamid verwendet wird.
  7. 7« Verfahren nach einem der vorhergehenden. Ansprüche, dadurch gekennzeichnet, daß2l-Chloroäthyl-3-(p7ridyl)-propyläther verwendet wird..
  8. 8. 4-(A1-Pyridyl)-tetrahydropyran.
    9· 4-(3'-Pyridyl)-tetrahydropyran.
    . h-(2»-Pyridyl)-tetrahydropyran.
    8098AS/09'93
DE19691967049 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen Withdrawn DE1967049A1 (de)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
GB1300868 1968-03-18
GB46736/71A GB1268194A (en) 1968-03-18 1968-03-18 Pyridine derivatives and their manufacture
GB2577368 1968-05-29
GB46739/71A GB1268196A (en) 1968-03-18 1968-05-29 Pyridine derivatives and their manufacture
GB6071668 1968-12-20
GB6071468 1968-12-20
GB6071568 1968-12-20
GB4673771 1968-12-20
GB246/69A GB1268191A (en) 1968-03-18 1969-01-02 Process for the manufacture of bipyridyls
US17417571A 1971-08-23 1971-08-23
US412093A US3873555A (en) 1968-03-18 1973-11-02 Process for the manufacture of bipyridyls

Publications (1)

Publication Number Publication Date
DE1967049A1 true DE1967049A1 (de) 1976-11-04

Family

ID=27581625

Family Applications (4)

Application Number Title Priority Date Filing Date
DE19691967049 Withdrawn DE1967049A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen
DE1913732A Expired DE1913732C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE1967047A Expired DE1967047C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967048 Withdrawn DE1967048A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

Family Applications After (3)

Application Number Title Priority Date Filing Date
DE1913732A Expired DE1913732C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE1967047A Expired DE1967047C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967048 Withdrawn DE1967048A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

Country Status (9)

Country Link
US (2) US3651071A (de)
AT (5) AT295535B (de)
BE (1) BE729987A (de)
CH (6) CH540255A (de)
DE (4) DE1967049A1 (de)
FR (1) FR2004163A1 (de)
GB (4) GB1268194A (de)
NL (1) NL167689C (de)
SE (2) SE394111B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03135978A (ja) * 1989-08-08 1991-06-10 Merck Sharp & Dohme Ltd 置換ピリジン、その製法、処方並びに痴呆症における使用法
DE19536652A1 (de) * 1995-09-30 1997-04-10 Judit Kirschke Kompresse zur Wärmetherapie unter Verwendung von temperaturregulierendem und/oder heilendem und/oder beschwerdelinderndem Material
JP4603646B2 (ja) * 1999-11-15 2010-12-22 富士フイルムファインケミカルズ株式会社 新規なジピリジル誘導体
DE602005023279D1 (de) 2004-03-02 2010-10-14 Dainippon Sumitomo Pharma Co Benzothiazin-3-one verbindung und zwischenprodukt dafür
JP5235947B2 (ja) * 2010-07-30 2013-07-10 富士フイルムファインケミカルズ株式会社 新規なジピリジル誘導体

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL131727C (de) * 1963-08-08 1900-01-01

Also Published As

Publication number Publication date
CH542222A (de) 1973-11-15
CH530997A (de) 1972-11-30
CH538506A (de) 1973-08-15
NL167689B (nl) 1981-08-17
US3651071A (en) 1972-03-21
GB1268196A (en) 1972-03-22
GB1268191A (en) 1972-03-22
AT289797B (de) 1971-05-10
DE1913732C3 (de) 1982-04-15
SE394111B (sv) 1977-06-06
AT292704B (de) 1971-09-10
DE1913732B2 (de) 1981-04-02
SE392468B (sv) 1977-03-28
AT292705B (de) 1971-09-10
DE1967047A1 (de) 1976-10-07
AT295535B (de) 1972-01-10
CH540255A (de) 1973-10-15
DE1967047B2 (de) 1980-05-14
DE1967048A1 (de) 1976-11-04
GB1268194A (en) 1972-03-22
DE1967047C3 (de) 1981-01-22
BE729987A (de) 1969-09-17
FR2004163A1 (de) 1969-11-21
CH532051A (de) 1972-12-31
NL167689C (nl) 1982-01-18
NL6903976A (de) 1969-09-22
AT292706B (de) 1971-09-10
CH540910A (de) 1973-10-15
GB1268195A (en) 1972-03-22
US3873555A (en) 1975-03-25
DE1913732A1 (de) 1970-02-19

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