CA1050542A - Procede pour la preparation de benzylamines - Google Patents

Procede pour la preparation de benzylamines

Info

Publication number: CA1050542A
Authority: CA; Canada
Prior art keywords: compound; amino; acid addition; formula; preparation
Prior art date: 1973-09-08
Legal status (The legal status 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 status listed.): Expired

Application number

CA208,640A

Other languages

English (en)

Other versions

CA208640S (en

Inventor

Johannes Keck

Gerd Kruger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

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.)

1973-09-08

Filing date

1974-09-06

Publication date

1979-03-13

1973-09-08 Priority claimed from DE19732345443 external-priority patent/DE2345443C3/de

1974-09-06 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1979-03-13 Application granted granted Critical

1979-03-13 Publication of CA1050542A publication Critical patent/CA1050542A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims abstract description 8
GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical class NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
238000006243 chemical reaction Methods 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
-1 hydroxycyclohexyl Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
235000013350 formula milk Nutrition 0.000 claims 5
230000000954 anitussive effect Effects 0.000 abstract description 2
230000001766 physiological effect Effects 0.000 abstract description 2
MWUVUHYPGPVVOB-UHFFFAOYSA-N 2-(phenoxymethyl)aniline Chemical compound NC1=CC=CC=C1COC1=CC=CC=C1 MWUVUHYPGPVVOB-UHFFFAOYSA-N 0.000 abstract 1
150000001412 amines Chemical class 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000203 mixture Substances 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
125000003118 aryl group Chemical group 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
KFYUETCWLHHCEE-UHFFFAOYSA-N 2-[2-[2-(2-amino-6-chlorophenyl)ethoxy]ethyl]-3-chloroaniline Chemical compound NC1=C(CCOCCC2=C(C=CC=C2Cl)N)C(=CC=C1)Cl KFYUETCWLHHCEE-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
108010077895 Sarcosine Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
UCDKONUHZNTQPY-UHFFFAOYSA-N bromhexine hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N UCDKONUHZNTQPY-UHFFFAOYSA-N 0.000 description 1
125000006278 bromobenzyl group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
RRKODOZNUZCUBN-UHFFFAOYSA-N cycloocta-1,3-diene Chemical compound C1CCC=CC=CC1 RRKODOZNUZCUBN-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA208,640A 1973-09-08 1974-09-06 Procede pour la preparation de benzylamines Expired CA1050542A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732345443 DE2345443C3 (de)		1973-09-08	Verfahren zur Herstellung von 2-Amino-benzylaminen

Publications (1)

Publication Number	Publication Date
CA1050542A true CA1050542A (fr)	1979-03-13

Family

ID=5892074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA208,640A Expired CA1050542A (fr)	1973-09-08	1974-09-06	Procede pour la preparation de benzylamines

Country Status (14)

Country	Link
JP (1)	JPS594413B2 (fr)
AT (1)	AT327875B (fr)
BG (1)	BG23896A3 (fr)
CA (1)	CA1050542A (fr)
CH (1)	CH612662A5 (fr)
CS (1)	CS167212B2 (fr)
DK (2)	DK473074A (fr)
ES (1)	ES429698A2 (fr)
FI (1)	FI60551C (fr)
HU (1)	HU167685B (fr)
NL (1)	NL7410820A (fr)
PL (1)	PL91734B1 (fr)
SE (2)	SE439158B (fr)
YU (1)	YU37109B (fr)

1974
- 1974-08-02 FI FI2317/74A patent/FI60551C/fi active
- 1974-08-08 AT AT650974A patent/AT327875B/de not_active IP Right Cessation
- 1974-08-13 NL NL7410820A patent/NL7410820A/xx not_active Application Discontinuation
- 1974-08-31 ES ES429698A patent/ES429698A2/es not_active Expired
- 1974-09-05 YU YU2392/74A patent/YU37109B/xx unknown
- 1974-09-05 JP JP49102496A patent/JPS594413B2/ja not_active Expired
- 1974-09-06 CH CH1218774A patent/CH612662A5/xx not_active IP Right Cessation
- 1974-09-06 SE SE7411313A patent/SE439158B/xx not_active IP Right Cessation
- 1974-09-06 CA CA208,640A patent/CA1050542A/fr not_active Expired
- 1974-09-06 HU HUTO979A patent/HU167685B/hu unknown
- 1974-09-06 CS CS6151A patent/CS167212B2/cs unknown
- 1974-09-06 DK DK473074A patent/DK473074A/da not_active Application Discontinuation
- 1974-09-07 PL PL1974173960A patent/PL91734B1/pl unknown
- 1974-09-07 BG BG7400027655A patent/BG23896A3/xx unknown
1976
- 1976-12-22 DK DK579676A patent/DK579676A/da not_active Application Discontinuation
1977
- 1977-09-01 SE SE7709868A patent/SE427178B/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE7709868L (sv)	1977-09-01
SE439158B (sv)	1985-06-03
CH612662A5 (en)	1979-08-15
YU239274A (en)	1983-04-27
JPS594413B2 (ja)	1984-01-30
ES429698A2 (es)	1977-07-01
JPS5053347A (fr)	1975-05-12
DE2345443A1 (de)	1975-03-27
YU37109B (en)	1984-08-31
FI60551B (fi)	1981-10-30
DK473074A (fr)	1975-05-05
AT327875B (de)	1976-02-25
PL91734B1 (fr)	1977-03-31
FI60551C (fi)	1982-02-10
DK579676A (da)	1976-12-22
CS167212B2 (fr)	1976-04-29
HU167685B (fr)	1975-11-28
NL7410820A (nl)	1975-03-11
SE7411313L (fr)	1975-03-10
SE427178B (sv)	1983-03-14
ATA650974A (de)	1975-05-15
BG23896A3 (bg)	1977-11-10
DE2345443B2 (de)	1976-01-02
FI231774A7 (fr)	1975-03-09

Publication	Publication Date	Title
FI71126C (fi)	1986-11-24	Foerfarande foer framstaellning av n-(1-alkyl- eller allyl -2-pyrrolidinylmetyl)-2-metoxi-4-amino- -5-alkylsulfonylbensamider
US5512677A (en)	1996-04-30	3-substituted methyl-2,3-dihydroimidazo 1,2-c!quinazoline derivatives, the preparation and use thereof
GB2060618A (en)	1981-05-07	3-Aryl-3-Aryloxypropylamines
CH521356A (de)	1972-04-15	Verfahren zur Herstellung von aromatischen Äthern
US3956262A (en)	1976-05-11	Triazenoimidazoles
JPS5817454B2 (ja)	1983-04-07	アルキル化ヒドロキシルアミン及びその製法
US4061647A (en)	1977-12-06	Thiazolidine derivatives
EP0055450B1 (fr)	1984-12-05	Dérivés du pyrazoloindazole, procédé pour leur préparation et composition pharmaceutique les contenant
GB1567958A (en)	1980-05-21	Piperazine and piperazine homologue derivatives and preparation and use thereof
CA2368815A1 (fr)	2000-10-26	Nouvelle synthese et cristallisation de composes contenant de la piperazine
EP0056866B1 (fr)	1985-06-19	Dérivés phénylpipérazines d'hétarylphénoles et d'hétarylanilines, leur préparation et leurs compositions pharmaceutiques
CA1050542A (fr)	1979-03-13	Procede pour la preparation de benzylamines
US4656180A (en)	1987-04-07	Diamine derivatives and pharmaceutical preparations containing these compounds
JPS6026154B2 (ja)	1985-06-21	塩基性オキサジン染料の製造法
US4314082A (en)	1982-02-02	Derivatives of 2-amino-6,7-dihydroxytetrahydro naphthalene (ADTN)
Horning et al.	1973	Synthesis of phenols from diazonium tetrafluoroborates; a useful modification
PL84351B1 (fr)	1976-03-31
US3898224A (en)	1975-08-05	1,6,7,8-Tetrahydro-4-oxo-4H-pyrido {8 1,2-A{9 pyrimidine-9-carboalkoxy compounds
GB1592295A (en)	1981-07-01	Sulphamoylbenzoic acids
US4118501A (en)	1978-10-03	Thiazolidine derivatives
US3141893A (en)	1964-07-21	4-amino-coumarins
GB2068963A (en)	1981-08-19	Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents and relevant preparation processes
US4156735A (en)	1979-05-29	Thiazolidine derivatives
ROBINSON et al.	1936	The synthesis of substituted 5, 6-benzocinchoninic acids by the Doebner and by the Pfitzinger reactions
PT79456B (en)	1986-11-14	Heterocyclic compounds