JPS594413B2 - ２−アミノ−ベンジルアミンの新規製造方法 - Google Patents
２−アミノ−ベンジルアミンの新規製造方法Info
- Publication number
- JPS594413B2 JPS594413B2 JP49102496A JP10249674A JPS594413B2 JP S594413 B2 JPS594413 B2 JP S594413B2 JP 49102496 A JP49102496 A JP 49102496A JP 10249674 A JP10249674 A JP 10249674A JP S594413 B2 JPS594413 B2 JP S594413B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- amino
- formulas
- benzylamine
- methyl
- 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
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- -1 hydroxycyclohexyl Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 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
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 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 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- SIORJVCVMABMKE-UHFFFAOYSA-N 2,4-dibromo-6-(phenoxymethyl)aniline Chemical compound NC1=C(COC2=CC=CC=C2)C=C(C=C1Br)Br SIORJVCVMABMKE-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 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
- 239000008096 xylene Substances 0.000 description 2
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-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
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108010002352 Interleukin-1 Proteins 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 150000002148 esters Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 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
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732345443 DE2345443C3 (de) | 1973-09-08 | Verfahren zur Herstellung von 2-Amino-benzylaminen | |
| DE2345443 | 1973-09-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5053347A JPS5053347A (en, 2012) | 1975-05-12 |
| JPS594413B2 true JPS594413B2 (ja) | 1984-01-30 |
Family
ID=5892074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49102496A Expired JPS594413B2 (ja) | 1973-09-08 | 1974-09-05 | ２−アミノ−ベンジルアミンの新規製造方法 |
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 |
| CA1050542A (en) | 1979-03-13 |
| 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 |
| DE2345443B2 (de) | 1976-01-02 |
| YU239274A (en) | 1983-04-27 |
| ES429698A2 (es) | 1977-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1128526A (en) | 3,4-diarylisoxazol-5-acetic acids | |
| JPS6354321A (ja) | 血糖降下剤 | |
| JPS6056143B2 (ja) | アミジン誘導体ならびにその製造法 | |
| IMMEDIATA et al. | β-Naphthyl derivatives of ethanolamine and n-substituted ethanolamines | |
| US2868833A (en) | Aliphatic diamines and salts thereof | |
| JPH05320103A (ja) | プロパンアミンおよびその治療用とくに止瀉用医薬組成物 | |
| JPS594413B2 (ja) | ２−アミノ−ベンジルアミンの新規製造方法 | |
| JPS6026154B2 (ja) | 塩基性オキサジン染料の製造法 | |
| JPS63145286A (ja) | 二環性イミダゾ−ル誘導体 | |
| US3141893A (en) | 4-amino-coumarins | |
| US3138636A (en) | Anthranilic acid derivatives | |
| CA1138897A (en) | Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents, and relevant preparation processes | |
| GB2027028A (en) | Preparing o-(2,6-dichloroanilino)phenylacetic acid | |
| US4127666A (en) | Disubstituted 2,5-benzamides and pharmaceutical compositions containing the same | |
| US2695293A (en) | N, n'-substituted diamine compounds and method of making the same | |
| US3109022A (en) | Nu-aryl anthranilic acids | |
| JPS6127977A (ja) | ４，５‐ジヒドロ‐３，３‐ジフエニル‐４‐ヒドロカルビルアミノメチルフラン‐２（３ｈ）‐オン | |
| US3322775A (en) | Quaternary ammonium salts of [4-(3-aminoalkanoyl) phenoxy] alkanoic acids | |
| JPS58177992A (ja) | イソキサゾ−ル−〔５，４−ｂ〕−ピリジン類 | |
| JPS5817456B2 (ja) | ２− アシルアミノ − ベンジルアミンルイノセイゾウホウホウ | |
| JPS5944313B2 (ja) | インダゾ−ル誘導体の製法 | |
| JPS61183263A (ja) | ピロリジン誘導体の製造方法 | |
| JPH03215488A (ja) | ピリミドベンズイミダゾール誘導体 | |
| DE2554863C2 (de) | Thiazolinylidenaminophenylpropionsäure-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| JPS61118371A (ja) | 新規ピラゾロン誘導体およびその製造法 |