CA1050542A - Process for the preparation of 2-amino-benzylamines - Google Patents
Process for the preparation of 2-amino-benzylaminesInfo
- Publication number
- CA1050542A CA1050542A CA208,640A CA208640A CA1050542A CA 1050542 A CA1050542 A CA 1050542A CA 208640 A CA208640 A CA 208640A CA 1050542 A CA1050542 A CA 1050542A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- amino
- acid addition
- formula
- preparation
- Prior art date
- 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
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)
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 (en) | 1979-03-13 |
Family
ID=5892074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA208,640A Expired CA1050542A (en) | 1973-09-08 | 1974-09-06 | Process for the preparation of 2-amino-benzylamines |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS594413B2 (en, 2012) |
| AT (1) | AT327875B (en, 2012) |
| BG (1) | BG23896A3 (en, 2012) |
| CA (1) | CA1050542A (en, 2012) |
| CH (1) | CH612662A5 (en, 2012) |
| CS (1) | CS167212B2 (en, 2012) |
| DK (2) | DK473074A (en, 2012) |
| ES (1) | ES429698A2 (en, 2012) |
| FI (1) | FI60551C (en, 2012) |
| HU (1) | HU167685B (en, 2012) |
| NL (1) | NL7410820A (en, 2012) |
| PL (1) | PL91734B1 (en, 2012) |
| SE (2) | SE439158B (en, 2012) |
| YU (1) | YU37109B (en, 2012) |
-
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 DK DK473074A patent/DK473074A/da not_active Application Discontinuation
- 1974-09-06 CA CA208,640A patent/CA1050542A/en not_active Expired
- 1974-09-06 CS CS6151A patent/CS167212B2/cs unknown
- 1974-09-06 SE SE7411313A patent/SE439158B/xx not_active IP Right Cessation
- 1974-09-06 HU HUTO979A patent/HU167685B/hu unknown
- 1974-09-07 BG BG7400027655A patent/BG23896A3/xx unknown
- 1974-09-07 PL PL1974173960A patent/PL91734B1/pl 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 |
| SE7411313L (en, 2012) | 1975-03-10 |
| FI60551C (fi) | 1982-02-10 |
| DK473074A (en, 2012) | 1975-05-05 |
| DE2345443A1 (de) | 1975-03-27 |
| JPS5053347A (en, 2012) | 1975-05-12 |
| CS167212B2 (en, 2012) | 1976-04-29 |
| FI60551B (fi) | 1981-10-30 |
| FI231774A7 (en, 2012) | 1975-03-09 |
| DK579676A (da) | 1976-12-22 |
| YU37109B (en) | 1984-08-31 |
| NL7410820A (nl) | 1975-03-11 |
| ATA650974A (de) | 1975-05-15 |
| CH612662A5 (en) | 1979-08-15 |
| SE427178B (sv) | 1983-03-14 |
| SE439158B (sv) | 1985-06-03 |
| PL91734B1 (en, 2012) | 1977-03-31 |
| AT327875B (de) | 1976-02-25 |
| HU167685B (en, 2012) | 1975-11-28 |
| BG23896A3 (bg) | 1977-11-10 |
| JPS594413B2 (ja) | 1984-01-30 |
| DE2345443B2 (de) | 1976-01-02 |
| YU239274A (en) | 1983-04-27 |
| ES429698A2 (es) | 1977-07-01 |
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