CH485653A - Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate - Google Patents

Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate

Info

Publication number: CH485653A
Authority: CH; Switzerland
Prior art keywords: dibenzo; aminoalkylated; acid; preparation; cycloheptene
Prior art date: 1967-07-24

Application number

CH1909169A

Other languages

German (de)

English (en)

Inventor

Hamish Dr Russel Jeff

Original Assignee

Wander Ag Dr A

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.)

1967-07-24

Filing date

1967-07-24

Publication date

1970-02-15

1967-07-24 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1967-07-24 Priority to CH1909169A priority Critical patent/CH485653A/de

1970-02-15 Publication of CH485653A publication Critical patent/CH485653A/de

Links

238000000034 method Methods 0.000 title claims description 5
QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
-1 psychosedativa Substances 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
229940125688 antiparkinson agent Drugs 0.000 description 1
239000000939 antiparkinson agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000001933 cycloheptenes Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1909169A 1967-07-24 1967-07-24 Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate CH485653A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1909169A CH485653A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1909169A CH485653A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1050167A CH485650A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate

Publications (1)

Publication Number	Publication Date
CH485653A true CH485653A (de)	1970-02-15

Family

ID=4363890

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH1909169A CH485653A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1050167A CH485650A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1908969A CH485651A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1909069A CH485652A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH1050167A CH485650A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1908969A CH485651A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH1909069A CH485652A (de)	1967-07-24	1967-07-24	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate

Country Status (7)

Country	Link
BE (1)	BE718434A (fr)
CH (4)	CH485653A (fr)
DE (1)	DE1768706A1 (fr)
FR (1)	FR7907M (fr)
GB (1)	GB1185277A (fr)
IL (1)	IL30368A0 (fr)
NL (1)	NL6809838A (fr)

1967
- 1967-07-24 CH CH1909169A patent/CH485653A/de not_active IP Right Cessation
- 1967-07-24 CH CH1050167A patent/CH485650A/de not_active IP Right Cessation
- 1967-07-24 CH CH1908969A patent/CH485651A/de not_active IP Right Cessation
- 1967-07-24 CH CH1909069A patent/CH485652A/de not_active IP Right Cessation
1968
- 1968-06-21 DE DE19681768706 patent/DE1768706A1/de active Pending
- 1968-07-11 NL NL6809838A patent/NL6809838A/xx unknown
- 1968-07-15 GB GB33608/68A patent/GB1185277A/en not_active Expired
- 1968-07-15 IL IL30368A patent/IL30368A0/xx unknown
- 1968-07-18 FR FR159699A patent/FR7907M/fr not_active Expired
- 1968-07-23 BE BE718434D patent/BE718434A/xx unknown

Also Published As

Publication number	Publication date
IL30368A0 (en)	1968-09-26
GB1185277A (en)	1970-03-25
CH485651A (de)	1970-02-15
FR7907M (fr)	1970-05-11
NL6809838A (fr)	1969-01-28
CH485652A (de)	1970-02-15
BE718434A (fr)	1969-01-23
CH485650A (de)	1970-02-15
DE1768706A1 (de)	1971-11-18

Legal Events

Date	Code	Title	Description
1971-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2139084C3 (de)	1979-03-01	Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen
CH240363A (de)	1945-12-15	Verfahren zur Herstellung von N-(y,y-Diphenyl-allyl)-piperidin.
DE883154C (de)	1953-07-16	Verfahren zur Umlagerung von Chinaalkaloiden
CH485651A (de)	1970-02-15	Verfahren zur Herstellung 10-aminoalkylierter 5H-Dibenzo(a,d)-cycloheptenderivate
CH250806A (de)	1947-09-15	Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates.
AT205037B (de)	1959-08-25	Verfahren zur Herstellung eines neuen Thioxanthen-Derivates
AT222655B (de)	1962-08-10	Verfahren zur Herstellung von neuen Derivaten von 5H- Dibenzo [b, f] azepinen bzw. deren Salzen oder quaternären Ammoniumverbindungen
AT235831B (de)	1964-09-25	Verfahren zur Herstellung von neuen Estern basischer Carbinole und ihren Säureadditionssalzen
AT217026B (de)	1961-09-11	Verfahren zur Herstellung von neuen α-Aminoisobutyrophenonverbindungen und deren Säureadditionssalzen
DE913896C (de)	1954-06-21	Verfahren zur Herstellung von 6-Methyl-8-oxy-ergolin
CH360067A (de)	1962-02-15	Verfahren zur Herstellung von neuen Scopinäthern
AT283308B (de)	1970-08-10	Verfahren zur herstellung von neuen 5-aminomethylierten 5 h-dibenzo<a,d>cycloheptenen und ihren salzen
AT225359B (de)	1963-01-10	Verfahren zur Herstellung des neuen 17-β-Oxy-17-α-methylandrostan-(3, 2, -c)-iso-oxazols
AT134629B (de)	1933-09-11	Verfahren zur Darstellung von Aminoalkoholen.
CH481870A (de)	1969-11-30	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten
CH435250A (de)	1967-05-15	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane
CH235916A (de)	1944-12-31	Verfahren zur Hydratisierung eines Acetylenderivates der Cyclopentanopolyhydrophenanthren-Reihe.
CH260994A (de)	1949-04-15	Verfahren zur Herstellung der Vitamin-A-Säure.
CH299597A (de)	1954-06-15	Verfahren zur Darstellung eines Amins der Lysergsäurereihe.
CH300418A (de)	1954-07-31	Verfahren zur Herstellung eines neuen Thioäthers.
CH333016A (de)	1958-09-30	Verfahren zur Herstellung neuer Piperidine
CH302068A (de)	1954-09-30	Verfahren zur Herstellung eines neuen Aminoacetessigsäureäthylesterderivates.
CH275687A (de)	1951-05-31	Verfahren zur Herstellung eines neuen Benzoesäureesters.
CH258172A (de)	1948-11-15	Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates.
CH250809A (de)	1947-09-15	Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates.