CH481869A - Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten - Google Patents

Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten

Info

Publication number: CH481869A
Authority: CH; Switzerland
Prior art keywords: hydrochloride; chs; hydrogen atom; alkyl group; dibenzo
Prior art date: 1966-05-10

Application number

CH1716968A

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.)

1966-05-10

Filing date

1966-05-10

Publication date

1969-11-30

1966-05-10 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1966-05-10 Priority to CH1716968A priority Critical patent/CH481869A/de

1969-11-30 Publication of CH481869A publication Critical patent/CH481869A/de

Links

238000000034 method Methods 0.000 title claims description 7
PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical class C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
238000002844 melting Methods 0.000 claims description 5
230000008018 melting Effects 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 4
150000003141 primary amines Chemical class 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
-1 hydrohalic acids Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material 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
KRGZWDPNVIINFY-UHFFFAOYSA-N 1-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)-n-methylmethanamine Chemical compound C1CC2=CC=CC=C2C(CNC)C2=CC=CC=C21 KRGZWDPNVIINFY-UHFFFAOYSA-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
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
150000001299 aldehydes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
238000005905 alkynylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 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
150000001412 amines Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229960003965 antiepileptics Drugs 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
239000003638 chemical reducing agent Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
150000001933 cycloheptenes Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 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
238000004519 manufacturing process Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

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)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1716968A 1966-05-10 1966-05-10 Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten CH481869A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1716968A CH481869A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1716968A CH481869A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten
CH678166A CH473759A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten

Publications (1)

Publication Number	Publication Date
CH481869A true CH481869A (de)	1969-11-30

Family

ID=4314928

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1716968A CH481869A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten
CH1716868A CH481055A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten
CH678166A CH473759A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1716868A CH481055A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten
CH678166A CH473759A (de)	1966-05-10	1966-05-10	Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo (a,d)-cyclohepten-Derivaten

Country Status (12)

Country	Link
AT (3)	AT283312B (cs)
BE (1)	BE698198A (cs)
CH (3)	CH481869A (cs)
CS (4)	CS154229B2 (cs)
DE (1)	DE1643212A1 (cs)
ES (1)	ES340257A1 (cs)
FI (1)	FI47348C (cs)
FR (1)	FR6502M (cs)
GB (1)	GB1170798A (cs)
GR (1)	GR36291B (cs)
NL (1)	NL6706480A (cs)
NO (1)	NO122246B (cs)

1966
- 1966-05-10 CH CH1716968A patent/CH481869A/de not_active IP Right Cessation
- 1966-05-10 CH CH1716868A patent/CH481055A/de not_active IP Right Cessation
- 1966-05-10 CH CH678166A patent/CH473759A/de not_active IP Right Cessation
1967
- 1967-05-03 FI FI671285A patent/FI47348C/fi active
- 1967-05-03 DE DE19671643212 patent/DE1643212A1/de active Pending
- 1967-05-05 GB GB20979/67A patent/GB1170798A/en not_active Expired
- 1967-05-08 GR GR670136291A patent/GR36291B/el unknown
- 1967-05-08 ES ES340257A patent/ES340257A1/es not_active Expired
- 1967-05-09 AT AT870769A patent/AT283312B/de not_active IP Right Cessation
- 1967-05-09 NO NO168071A patent/NO122246B/no unknown
- 1967-05-09 BE BE698198D patent/BE698198A/xx unknown
- 1967-05-09 NL NL6706480A patent/NL6706480A/xx unknown
- 1967-05-09 AT AT434967A patent/AT283303B/de not_active IP Right Cessation
- 1967-05-09 AT AT870569A patent/AT283311B/de not_active IP Right Cessation
- 1967-05-10 FR FR105888A patent/FR6502M/fr not_active Expired
- 1967-05-10 CS CS281170*1A patent/CS154229B2/cs unknown
- 1967-05-10 CS CS281270*1A patent/CS154230B2/cs unknown
- 1967-05-10 CS CS281370*1A patent/CS154231B2/cs unknown
- 1967-05-10 CS CS337867A patent/CS154228B2/cs unknown

Also Published As

Publication number	Publication date
CH473759A (de)	1969-06-15
CS154231B2 (cs)	1974-03-29
GR36291B (el)	1969-01-20
ES340257A1 (es)	1968-09-01
CS154228B2 (cs)	1974-03-29
CH481055A (de)	1969-11-15
NL6706480A (cs)	1967-11-13
FI47348B (cs)	1973-07-31
CS154230B2 (cs)	1974-03-29
AT283312B (de)	1970-08-10
GB1170798A (en)	1969-11-19
CS154229B2 (cs)	1974-03-29
AT283311B (de)	1970-08-10
BE698198A (cs)	1967-11-09
FR6502M (cs)	1968-12-02
NO122246B (cs)	1971-06-07
FI47348C (fi)	1973-11-12
DE1643212A1 (de)	1971-03-11
AT283303B (de)	1970-08-10

Legal Events

Date	Code	Title	Description
1980-03-14	PL	Patent ceased

Publication	Publication Date	Title
DE2351281C3 (de)	1981-07-30	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung
CH481869A (de)	1969-11-30	Verfahren zur Herstellung von 5-aminomethylierten 10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-Derivaten
AT283308B (de)	1970-08-10	Verfahren zur herstellung von neuen 5-aminomethylierten 5 h-dibenzo<a,d>cycloheptenen und ihren salzen
CH356121A (de)	1961-08-15	Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren
DE1670152C2 (de)	1983-10-27	N-substituierte Granatanol-tropasäureester und ein Verfahren zu ihrer Herstellung
DE945449C (de)	1956-07-12	Verfahren zur Herstellung von 2-Methyl-4-cyclohexyl-6-methyl-aminomethylphenol
DE1793612C (cs)	1973-03-01
DE287802C (cs)
DE1158083B (de)	1963-11-28	Verfahren zur Herstellung basisch substituierter Phenylacetonitrile
CH481870A (de)	1969-11-30	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten
AT220619B (de)	1962-04-10	Verfahren zur Herstellung von Aminoalkylbenzhydryläthern
AT265259B (de)	1968-10-10	Verfahren zur Herstellung von neuen rechtsdrehenden und linksdrehenden Formen von 1-(β-Hydroxy- oder -Halogen-äthyl)-diphenylmethyl-piperidinen und ihren Salzen
AT231455B (de)	1964-01-27	Verfahren zur Herstellung von neuen Diazepinderivaten
AT283307B (de)	1970-08-10	Verfahren zur herstellung von neuen 5-aminomethylierten 5 h-dibenzo<a,d>cycloheptenen und ihren salzen
AT280976B (de)	1970-05-11	Verfahren zur Herstellung von neuen Alkylendiaminderivaten und von deren Säureadditionssalzen
AT211823B (de)	1960-11-10	Verfahren zur Herstellung von neuen Aryloxyessigsäureamiden
AT243445B (de)	1965-11-10	Verfahren zur Herstellung von neuen, am Stickstoff substituierten 3-(Dibenzo-[a,d]-1, 4-cycloheptadien-5-yloxy)-nortropanen und von Salzen dieser Verbindungen
AT378191B (de)	1985-06-25	Verfahren zur herstellung neuer pyrogallolaether-derivate
AT208871B (de)	1960-05-10	Verfahren zur Herstellung von neuen N-substituierten Azepinen bzw. Dihydroazepinen
AT233019B (de)	1964-04-25	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
DE1493904C (de)	1972-07-27	Trifluormethylsubstituierte basische Phenylacetonitrile und Verfahren zu deren Herstellung
DE959097C (de)	1957-02-28	Verfahren zur Herstellung von basisch substituierten Diarylacetonitrilen
AT220144B (de)	1962-03-12	Verfahren zur Herstellung von neuen tertiären Aminen, sowie deren Säureadditions- und quaternären Ammoniumsalzen
AT219611B (de)	1962-02-12	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen und deren Salzen
AT233577B (de)	1964-05-11	Verfahren zur Herstellung neuer, basischer Phenoxazin-Derivate und ihrer Salze