DE1967048A1 - Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen - Google Patents

Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

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Publication number
DE1967048A1
DE1967048A1 DE19691967048 DE1967048A DE1967048A1 DE 1967048 A1 DE1967048 A1 DE 1967048A1 DE 19691967048 DE19691967048 DE 19691967048 DE 1967048 A DE1967048 A DE 1967048A DE 1967048 A1 DE1967048 A1 DE 1967048A1
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Prior art keywords
added
pyridyl
tetrahydropyrans
stirred
mixture
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DE19691967048
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English (en)
Inventor
Roy Dennis Bowden
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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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

Mappe 23930 - Dr. K/by
ICI Case MD 22902 B
IMPERIAL CHEMIG1.L TEIKBTRIES LTD. London, Großbritannien
Verfahren zur Herstellung: von 4-(Pyridyl)tetrahydropyranen
Die Erfindung "bezieht sich auf Pyridinderivate und ihre Herstellung*
Gemäß der Erfindung wird ein Verfahren zur, Herstellung von 4-(Pyridyl)tetrahydropyranen vorgeschlagen, welches dadurch ausgeführt wird, daß man dasentsprechende 3-(Pyridyl)pentandiol auf mindestens 250°C erhitzt. Das Erhitzen erfolgt vorzugsweise in Gegenwart eines Katalysators„
Die Temperatur, auf welche das Diol erhitzt wird, um es in den entsprechenden cyclischen Pyridylather umzuwandeln, beträgt mindestens 25O0C und vorzugsweise mindestens 3000C. Es wird insbesondere bevorzugt, eine Temperatur in der Größenordnung von 38O0C zu verwenden. Es reicht aus, das Diol einfach auf die gewünschte Temperatur zu erhitzen, aber es wird bevorzugt, die Erhitzung in Gegenwart eines Dehydrierungskatalysators, wie z.B. Aluminiumoxid, Siliciumdioxid, Siliciumdioxid—Aluminiumoxid oder Gemischen daraus zu erhitzen. Eine besonders zweckmäßige Technik besteht darin, das Diol in der Dampfphase durch ein Bett des Katalysators, der sich in einem Reaktionsrohr, wie z.B. einem Glasrohr, befindet, hindurchzuführen* Ggf. kann das Erhitzen unter überatmosphärischem Druck ausgeführt werden, in welchem Falle niedrigere Temperaturen für die Umwandlung nötig sind.
Die 4-(Pyridyl)tetrahydropyrane, die durch diese Reaktion gebildet werden, können durch Umsetzung in der Dampfphase mit Ammoniak in Bipyridyle umgewandelt werden. Die Reaktion wird vorzugsweise in Gegenwart von molekularem Sauerstoff, wie z.B. Sauerstoffgas, ausgeführt.
Die Erfindung wird durch die folgenden Beispiele näher erläutert.
BEISPIEL 1
Zu 3 1 gerührtem flüssigem Ammoniak wurden 0,1 g Eisen(III)-nitrat und dann 24 g Natriummetall in Form von 1 g wiegenden Stücken während eines Zeitraums von 4-0 min zugegeben. Zu der resultierenden Lösung wurden 46,6 g gamma-Picolin während eines Zeitraums von 3 min zugegeben. Während der nachfolgenden 2 st entwickelte sich eine tiefgelbe Farbe. 44,0 g flüssiges Äthylenoxid wurden zugesetzt,· und das Gemisch wurde weitere 8 st gerührt. Fun wurden 55 S festes Ammonrumchlorid in kleinen Mengen zugesetzt, und die Lösung wurde dann über
609845/0992
Nacht eindampfen gelassen. Der klebrige Rückstand, der 3-(4-Pyridyl)pentan-1,5-diol enthielt, wurde in Pyridin extrahiert, und das Pyridin wurde dann eingedampft. Das zurückbleibende öl würde in einer gleichen Menge heißem Wasser aufgelöst und auf ein Bett von Aluminiumoxid, das auf 38O0C erhitzt war, mit einer Geschwindigkeit von T ml/min tropfen gelassen, wobei als Trägergas ein Fluß von 300 ml/min Stickstoff verwendet wurde. Der Abstrom wurde kondensiert, und das Kondensat wurde in Tetrachlorkohlenstoff extrahiert. Abdampfen des Lösungsmittels und anschließende Destillation ergab 19 g 4-(4'-Pyridyl)tetrahydropyran. Die Umwandlung betrug 42 %, bezogen auf zugeführtes gamma-Picolin.
BEISPIELE .■;."■'■'-_.
Zu 300 ml gerührtem flüssigem Ammoniak wurden 50 mg Eisen(III)-nitrat und 1,2 g Natriummetall zugegeben. Das Gemisch wurde 30 min stehen gelassen, und dann wurden 4,7 g gamma~Picolin zugesetzt. Es entwickelte sich während der nachfolgenden 2 st eine tiefgelbe Parbe. 2,2 g gekühltes Äthylenoxid wurden dann zugesetzt, und das Gemisch wurde weitere 4 st gerührt, wobei eine lösung erhalten wurde, die mit "Lösung A" bezeichnet wurde. . ■ "■-". ;■■■■ Λ - ...■■ "■, -- . ■'"■■'.. -
Zu 200 ml gerührtem flüssigem Ammoniak wurden 50 mg Eisen(III)-nitrat und 1,2 g Natriummetall zugegeben. Das Gemisch wurde 30 min stehen gelassen und dann während eines Zeitraums von 2 min zur Lösung A zugegeben« Das Gemisch wurde weitere 4 st gerührt, worauf 6 g festes Ammoniumchlorid langsam zugegeben wurden. Das Lösungsmittel wurde über Nacht abdampfen gelassen, und der Rückstand wurde in 100 ml Methanol extrahiert und filtriert. ; . .
Das Filtrat, welches 3-(4-Pyridyl)pentan-1,5-diol enthielt, wurde mit einer Geschwindigkeit von 25 ml/st verdampft und in einem Strom aus Stickstoff trägergas (100 ml/min) durch
ein 10 cm hohes Bett aus 13 % Siliciumdioxid—Aluminiumoxid in einem Glasrohr, das einen Durchmesser von 2,5 cm und eine Temperatur von 3400C aufwies, hindurchgeführt. Der flüssige Reaktorabstrom wurde durch Gas/Elüssigkeits-Chromatografie analysiert. Er enthielt 4-(4-'-Pyridyl)tetrahydropyran (Umwandlung 62 %y,
BEISPIEL 3
Zu 300 ml gerührtem flüssigem Ammoniak wurden 50 mg Eisen(III)-nitrat und 2,0 g Kaliummetall zugegeben. Das Gemisch wurde 30 min stehen gelassen, worauf 4,7 g gamma-Picolin zugesetzt wurden. Es entwickelte sich während der nachfolgenden 2 st eine tiefgelbe Farbe. 2,2 g gekühltes Äthylenoxid wurden dann zugesetzt, und das Gemisch wurde weitere 4 st gerührt, wobei eine Lösung erhalten wurde, die mit "Lösung B" bezeichnet wurde.
Zu 200 ml gerührtem flüssigem Ammoniak wurden 50 mg Eisen(lll)-nitrat und 2,0 g Kaliummetall zugegeben. Das Gemisch wurde 30 min stehen gelassen und während eines Zeitraums von 2 min zur Lösung.B zugegeben. Das Gemisch wurde weitere 4 st gerührt., worauf 6 g festes Ammoniumchlorid langsam zugesetzt wurden. Das Lösungsmittel wurde über Nacht abdampfen gelassen, und der Rückstand wurde in 100 ml Methanol extrahiert und filtriert.
Das Filtrat wurde mit einer Geschwindigkeit von 25 ml/st verdampft und in einem Stickstoffträgergasstrom (100 ml/min) über ein 10 cm hohes Bett aus 13 % Siliciumdioxid-Aluminiumoxid geführt, das sich in einem Glasreaktionsrohr mit einer Temperatur von 340°C und einem Durchmesser, von 2,5 cm befand." Der flüssige Reaktorabstrom wurde durch Gas/Flüssigkeits-Chromatografie analysiert. Er enthielt 4-(4*-Pyridyl)tetrahydropyran. Die Umwandlung war 58 %■, bezogen auf zugeführtes gamma-Picolin.
- 4 «
6098A5/0992
BEISPIEL· 4- ϊ\ -
5 S 3-(4·'-Pyridyl)pentan-1,5-cLiol wurden bei einer Temperatur von mehr als 30O0C unter' atmo sphärischem Druck destilliert. Das Destillat wurde in Äther extrahiert» und die Lösung wurde mit Wasser gewaschen und über Magnesiumsulfat getrocknet. Abdampfen des Lösungsmittels und Destillation des .zurückbleibenden Öls ergab 2,2 g 4-(4-l-Pyridyl)tetrahydropyraiL. Die Umwandlung war 58 %^ bezogen auf zugeführtes

Claims (2)

  1. PATENTANSPRÜCHE;
    1* Verfahren zur Herstellung eines 4~(Pyridyl)tetrahydropyrans, dadurch gekennzeichnet, daß man das entsprechende 3-(Pyridyl)pentandiol auf eine Temperatur von mindestens 2500C erhitzt. ■
  2. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man das Diol in Gegenwart eines Dehydrierungskatalysators erhitzt.
    PATENTANWÄLTE
    «..FINCKE, OI PL - - ^
    - 6 SC98A5/0392
DE19691967048 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen Withdrawn DE1967048A1 (de)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
GB46736/71A GB1268194A (en) 1968-03-18 1968-03-18 Pyridine derivatives and their manufacture
GB1300868 1968-03-18
GB46739/71A GB1268196A (en) 1968-03-18 1968-05-29 Pyridine derivatives and their manufacture
GB2577368 1968-05-29
GB6071468 1968-12-20
GB6071568 1968-12-20
GB6071668 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
DE1967048A1 true DE1967048A1 (de) 1976-11-04

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ID=27581625

Family Applications (4)

Application Number Title Priority Date Filing Date
DE1913732A Expired DE1913732C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967049 Withdrawn DE1967049A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen
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 Before (3)

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

Country Status (9)

Country Link
US (2) US3651071A (de)
AT (5) AT292705B (de)
BE (1) BE729987A (de)
CH (6) CH538506A (de)
DE (4) DE1913732C3 (de)
FR (1) FR2004163A1 (de)
GB (4) GB1268194A (de)
NL (1) NL167689C (de)
SE (2) SE392468B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2022886A1 (en) * 1989-08-08 1991-02-09 Raymond Baker Substituted pyridines, their preparation, formulations and use in dementia
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
WO2005082872A1 (ja) * 2004-03-02 2005-09-09 Dainippon Sumitomo Pharma Co., Ltd. ベンゾチアジン－３－オン化合物及びその製造中間体
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
AT292705B (de) 1971-09-10
DE1913732C3 (de) 1982-04-15
GB1268194A (en) 1972-03-22
GB1268191A (en) 1972-03-22
FR2004163A1 (de) 1969-11-21
NL6903976A (de) 1969-09-22
DE1967047B2 (de) 1980-05-14
DE1913732A1 (de) 1970-02-19
NL167689B (nl) 1981-08-17
SE394111B (sv) 1977-06-06
CH530997A (de) 1972-11-30
AT292706B (de) 1971-09-10
CH540910A (de) 1973-10-15
AT295535B (de) 1972-01-10
NL167689C (nl) 1982-01-18
DE1913732B2 (de) 1981-04-02
CH540255A (de) 1973-10-15
CH532051A (de) 1972-12-31
US3873555A (en) 1975-03-25
BE729987A (de) 1969-09-17
DE1967049A1 (de) 1976-11-04
CH542222A (de) 1973-11-15
DE1967047C3 (de) 1981-01-22
US3651071A (en) 1972-03-21
AT292704B (de) 1971-09-10
CH538506A (de) 1973-08-15
GB1268196A (en) 1972-03-22
GB1268195A (en) 1972-03-22
DE1967047A1 (de) 1976-10-07
AT289797B (de) 1971-05-10
SE392468B (sv) 1977-03-28

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