CH450404A - Verfahren zur Herstellung homocyclischer Verbindungen - Google Patents

Verfahren zur Herstellung homocyclischer Verbindungen

Info

Publication number: CH450404A
Authority: CH; Switzerland
Prior art keywords: ethanol; naphthyl; tetrahydro; radical; isopropylamino
Prior art date: 1962-03-28

Application number

CH276967A

Other languages

German (de)

English (en)

Inventor

Howe Ralph

Harold Smith Leslie

Stuart Stephenson John

Original Assignee

Ici Ltd

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.)

1962-03-28

Filing date

1963-03-27

Publication date

1968-01-31

1963-03-27 Application filed by Ici Ltd filed Critical Ici Ltd

1968-01-31 Publication of CH450404A publication Critical patent/CH450404A/de

Links

150000001875 compounds Chemical class 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
-1 alkyl radical Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
230000008018 melting Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000002876 beta blocker Substances 0.000 description 1
229940030611 beta-adrenergic blocking agent Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH276967A 1962-03-28 1963-03-27 Verfahren zur Herstellung homocyclischer Verbindungen CH450404A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1187862A GB1005026A (en)	1962-03-28	1962-03-28	Naphthalene and indane derivatives

Publications (1)

Publication Number	Publication Date
CH450404A true CH450404A (de)	1968-01-31

Family

ID=9994330

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH276967A CH450404A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen
CH386463A CH444849A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen
CH276867A CH450403A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen
CH276767A CH450402A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH386463A CH444849A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen
CH276867A CH450403A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen
CH276767A CH450402A (de)	1962-03-28	1963-03-27	Verfahren zur Herstellung homocyclischer Verbindungen

Country Status (5)

Country	Link
CH (4)	CH450404A (da)
DE (1)	DE1468070A1 (da)
DK (4)	DK107161C (da)
GB (1)	GB1005026A (da)
SE (4)	SE311016B (da)

1962
- 1962-03-28 GB GB1187862A patent/GB1005026A/en not_active Expired
1963
- 1963-03-27 DK DK383964A patent/DK107161C/da active
- 1963-03-27 CH CH276967A patent/CH450404A/de unknown
- 1963-03-27 SE SE332563A patent/SE311016B/xx unknown
- 1963-03-27 CH CH386463A patent/CH444849A/de unknown
- 1963-03-27 DK DK384064A patent/DK107744C/da active
- 1963-03-27 DK DK383864A patent/DK107743C/da active
- 1963-03-27 CH CH276867A patent/CH450403A/de unknown
- 1963-03-27 DK DK138163A patent/DK107870C/da active
- 1963-03-27 CH CH276767A patent/CH450402A/de unknown
- 1963-03-28 DE DE19631468070 patent/DE1468070A1/de active Pending
1965
- 1965-02-03 SE SE138565A patent/SE314365B/xx unknown
- 1965-02-03 SE SE138465A patent/SE314364B/xx unknown
- 1965-02-03 SE SE138665A patent/SE314673B/xx unknown

Also Published As

Publication number	Publication date
DK107161C (da)	1967-05-01
CH450403A (de)	1968-01-31
DE1468070A1 (de)	1969-04-10
DK107870C (da)	1967-07-17
SE311016B (da)	1969-05-27
SE314673B (da)	1969-09-15
CH444849A (de)	1967-10-15
CH450402A (de)	1968-01-31
DK107744C (da)	1967-07-03
SE314365B (da)	1969-09-08
SE314364B (da)	1969-09-08
GB1005026A (en)	1965-09-22
DK107743C (da)	1967-07-03

Publication	Publication Date	Title
CH446289A (de)	1967-11-15	Verfahren zur Herstellung von Alkenderivaten
DE1242596B (de)	1967-06-22	Verfahren zur Herstellung des 1-Isopropylamino-2-hydroxy-3-(o-allyloxy-phenoxy)-propans
DE2351281C3 (de)	1981-07-30	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung
DE905246C (de)	1954-03-01	Verfahren zur Herstellung von Aminoalkoholen
DE971002C (de)	1958-11-27	Verfahren zur Herstellung von Thioxanthonen
DE2313625C2 (de)	1986-03-13	&alpha;-(Aminoalkyl)-4-hydroxy-3-(methylsulfonylmethyl)-benzylalkohole, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2148552A1 (de)	1972-04-06	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
AT361933B (de)	1981-04-10	Verfahren zur herstellung von neuen 5,11- -dihydro-6h-pyrido(2,3-b)(1,4)- benzodiazepin-6 -on-derivaten und ihren salzen
AT238180B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT221495B (de)	1962-05-25	Verfahren zur Herstellung von neuen Dibenzocycloheptanderivaten und deren Salzen bzw. quaternären Ammoniumverbindungen
DE711824C (de)	1941-10-11	Verfahren zur Darstellung substituierter Amine
AT282586B (de)	1970-07-10	Verfahren zur herstellung von neuem racemischem oder optisch aktivem (1-2'-nitrilophenoxy)-2-hydroxy-3-isopropylaminopropan und dessen salzen
DE1668964C3 (de)	1977-03-03	1-(2,3,5-Trimethyl-4-hydroxyphenoxy) -3-amino-2-propanol-Derivate und Verfahren zu deren Herstellung
AT225175B (de)	1963-01-10	Verfahren zur Herstellung neuer tertiärer Amine
DE871155C (de)	1953-03-19	Verfahren zur Herstellung von N-Monomethyl-ª-phenylaethylaminen
AT237601B (de)	1964-12-28	Verfahren zur Herstellung von 2-Phenyläthylaminderivaten
DE922650C (de)	1955-01-20	Verfahren zur Herstellung von Bibenzothiazolabkoemmlingen bzw. deren Salzen
DE951274C (de)	1956-10-25	Verfahren zur Herstellung von lokalanaesthetisch wirksamen tertiaeren N, N-Dialkylbenzylaminen
AT206439B (de)	1959-11-25	Verfahren zur Herstellung von neuen, racemischen oder optisch aktiven Piperidyl-(2)-arylmethanoläthern
CH444849A (de)	1967-10-15	Verfahren zur Herstellung homocyclischer Verbindungen
CH481875A (de)	1969-11-30	Verfahren zur Herstellung eines neuen Amins
CH474475A (de)	1969-06-30	Verfahren zur Herstellung neuer ungesättigter Amine
DE1668964A1 (de)	1972-04-13	Neue Trimethylhydrochinonderivate und Verfahren zur Herstellung derselben
CH465642A (de)	1968-11-30	Verfahren zur Herstellung neuer Amine
DE1770560A1 (de)	1971-11-04	Neue Aziridinderivate und Verfahren zu ihrer Herstellung