CH435250A - Verfahren zur Herstellung bicyclisch substituierter Aminoalkane - Google Patents

Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Info

Publication number: CH435250A
Authority: CH; Switzerland
Prior art keywords: formula; bicyclo; compounds; molecular weight; low molecular
Prior art date: 1962-06-09

Application number

CH638263A

Other languages

German (de)

English (en)

Inventor

Helmut Kraft

Wilfried Klavehn

Original Assignee

Knoll Ag

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.)

1962-06-09

Filing date

1963-05-21

Publication date

1967-05-15

1963-05-21 Application filed by Knoll Ag filed Critical Knoll Ag

1967-05-15 Publication of CH435250A publication Critical patent/CH435250A/de

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 4
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000002560 nitrile group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
239000008096 xylene Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003929 acidic solution Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
-1 sodium amine Chemical class 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
GYXWNSDLDXGMGU-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropan-1-amine Chemical compound CC(Cl)CN(C)C GYXWNSDLDXGMGU-UHFFFAOYSA-N 0.000 description 1
UPASYJUQYLIDMN-UHFFFAOYSA-N 3-bromo-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCBr UPASYJUQYLIDMN-UHFFFAOYSA-N 0.000 description 1
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH638263A 1962-06-09 1963-05-21 Verfahren zur Herstellung bicyclisch substituierter Aminoalkane CH435250A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEK46969A DE1284421B (de)	1962-06-09	1962-06-09	Bicyclisch substituierte Aminoalkane und Verfahren zu ihrer Herstellung

Publications (1)

Publication Number	Publication Date
CH435250A true CH435250A (de)	1967-05-15

Family

ID=7224390

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH638263A CH435250A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane
CH1638166A CH434241A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1638166A CH434241A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Country Status (3)

Country	Link
CH (2)	CH435250A (fr)
DE (1)	DE1284421B (fr)
FR (1)	FR2641M (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1130318A (fr) *	1978-10-11	1982-08-24	Peter M. Muller	Derives du cyclohexadiene

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1088484B (de) *	1958-03-10	1960-09-08	Bayer Ag	Verfahren zur Herstellung blutdruckwirksamer bicyclisch substituierter Carbinamine bzw. deren nicht toxischen Salzen
DE1110159B (de) *	1959-08-01	1961-07-06	Merck Ag E	Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen
BE598255A (fr) *	1959-12-19	1961-06-16	Knoll Ag	Nouvelles amines et leur préparation

1962
- 1962-06-09 DE DEK46969A patent/DE1284421B/de active Pending
1963
- 1963-05-21 CH CH638263A patent/CH435250A/de unknown
- 1963-05-21 CH CH1638166A patent/CH434241A/de unknown
- 1963-06-10 FR FR937603A patent/FR2641M/fr not_active Expired

Also Published As

Publication number	Publication date
FR2641M (fr)	1964-07-06
DE1284421B (de)	1968-12-05
CH434241A (de)	1967-04-30

Publication	Publication Date	Title
DE2351281C3 (de)	1981-07-30	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung
CH435250A (de)	1967-05-15	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane
AT239209B (de)	1965-03-25	Verfahren zur Herstellung von neuen bicyclisch substituierten Aminoalkanen sowie deren Salzen und quaternären Ammoniumverbindungen
CH396941A (de)	1965-08-15	Verfahren zur Herstellung neuer sekundärer Amine
AT162899B (de)	1949-04-25	Verfahren zur Darstellung von neuen Aminoalkyläthern von Alkoholen der aromatischaliphatischen Reihe
AT233581B (de)	1964-05-11	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT229292B (de)	1963-09-10	Verfahren zur Herstellung von neuen basisch substituierten Diphenylalkanderivaten und ihren Salzen
DE950550C (de)	1956-10-11	Verfahren zur Herstellung von basisch substituierten Phenylcycloalkenylpropanolen
DE1670053A1 (de)	1970-08-13	Verfahren zur Herstellung neuer Derivate des Morphanthridins
AT203497B (de)	1959-05-25	Verfahren zur Herstellung von neuen Diphenylmethan-derivaten, ihren Säuresalzen und quartären Salzen
AT275518B (de)	1969-10-27	Verfahren zur Herstellung von neuen in 4-Stellung substituierten 1-(4-Oxo-4-phenyl-butyl)-piperidinen sowie von deren Säureaddtionssalzen
AT210891B (de)	1960-08-25	Verfahren zur Herstellung von neuen Methylpiperidylpentanol-estern
AT235284B (de)	1964-08-25	Verfahren zur Herstellung neuer Indolderivate
AT248433B (de)	1966-07-25	Verfahren zur Herstellung von neuen ω-Phenyl-ω-pyridyl-alkylaminderivaten
AT256071B (de)	1967-08-10	Verfahren zur Herstellung von neuen Amino-halogen-benzylaminen und deren Additionssalzen mit Säuren
AT208869B (de)	1960-05-10	Verfahren zur Herstellung von neuen N-substituierten Azepinen
DE1445648C (de)	1972-05-18	Homopiperazindenvate
AT222104B (de)	1962-07-10	Verfahren zur Herstellung von neuen Cyclobutanderivaten
AT218506B (de)	1961-12-11	Verfahren zur Herstellung von basisch substituierten Carbinolen, sowie von ihren sterisch einheitlichen Razematen und deren optisch aktiven Komponenten und/oder ihren Säureadditionssalzen
AT339277B (de)	1977-10-10	Verfahren zur herstellung von neuen 11-amino-benzo(b) bicyclo (3,3,1)nona-3,6a(10a)dienen und deren saureadditionssalzen
AT219036B (de)	1962-01-10	Verfahren zur Herstellung von neuen 3-substituierten 1-Benzylindanen und deren Salzen
AT205037B (de)	1959-08-25	Verfahren zur Herstellung eines neuen Thioxanthen-Derivates
DE1768402C2 (de)	1983-04-07	Aminderivate des 5H-Dibenzo [a,d] cycloheptens und deren Verwendung bei der Bekämpfung von Gemütsdepressionen
AT219576B (de)	1962-02-12	Verfahren zur Herstellung von neuen basischen Äthern und deren Salzen
DE905244C (de)	1954-03-01	Verfahren zur Herstellung neuer Thioaether und ihrer quaternaeren und Saeuresalze