DE2338409A1 - Neues verfahren zur herstellung von 2-acylamino-benzylaminen - Google Patents
Neues verfahren zur herstellung von 2-acylamino-benzylaminenInfo
- Publication number
- DE2338409A1 DE2338409A1 DE19732338409 DE2338409A DE2338409A1 DE 2338409 A1 DE2338409 A1 DE 2338409A1 DE 19732338409 DE19732338409 DE 19732338409 DE 2338409 A DE2338409 A DE 2338409A DE 2338409 A1 DE2338409 A1 DE 2338409A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- derivs
- residue
- hal
- reaction
- 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.)
- Pending
Links
- -1 2-aminobenzyl Chemical group 0.000 title claims abstract description 14
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 title description 2
- 238000005576 amination reaction Methods 0.000 title 1
- 230000000954 anitussive effect Effects 0.000 title 1
- 239000003434 antitussive agent Substances 0.000 title 1
- 229940124584 antitussives Drugs 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 241000251730 Chondrichthyes Species 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 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 abstract description 2
- 150000004820 halides Chemical class 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid 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
- 150000007530 organic bases Chemical group 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KIQKWAUQWIPLSX-UHFFFAOYSA-N N-[3-chloro-2-[[methyl-(2-morpholin-2-yl-2-oxoethyl)amino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)C2CNCCO2)C)C(=CC=C1)Cl KIQKWAUQWIPLSX-UHFFFAOYSA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 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
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732338408 DE2338408C3 (de) | 1973-07-28 | Verfahren zur Herstellung von 2-Amino-benzylaminen | |
| DE19732338409 DE2338409A1 (de) | 1973-03-09 | 1973-07-28 | Neues verfahren zur herstellung von 2-acylamino-benzylaminen |
| AT68274*#A AT329020B (de) | 1973-03-09 | 1974-01-29 | Verfahren zur herstellung von halogenierten 2-aminobenzylaminen sowie deren saureadditionssalzen |
| FI316/74A FI60550C (fi) | 1973-03-09 | 1974-02-05 | Nytt foerfarande foer framstaellning av benzylaminer |
| NL7401880A NL7401880A (enrdf_load_stackoverflow) | 1973-03-09 | 1974-02-12 | |
| BG025828A BG21852A3 (bg) | 1973-03-09 | 1974-02-19 | Метод за получаване на бензиламини |
| ES423393A ES423393A1 (es) | 1973-03-09 | 1974-02-19 | Procedimiento para la preparacion de bencilaminas. |
| CS7400001636A CS180004B2 (en) | 1973-03-09 | 1974-03-06 | Method for production of benzylamines |
| CH317874A CH605617A5 (en) | 1973-03-09 | 1974-03-06 | 2-Aminobenzylamine derivs prepn. |
| SU2003605A SU512697A3 (ru) | 1973-03-09 | 1974-03-06 | Способ получени бензиламинов |
| HUTO956A HU167188B (enrdf_load_stackoverflow) | 1973-03-09 | 1974-03-07 | |
| YU60274A YU37107B (en) | 1973-03-09 | 1974-03-07 | Process for the preparation of 2-amino-benzylamines |
| SE7403159A SE434942B (sv) | 1973-03-09 | 1974-03-08 | Nytt forfarande for framstellning av bensylaminer |
| NO740820A NO138406C (no) | 1973-03-09 | 1974-03-08 | Fremgangsmaate for fremstilling av benzylaminer |
| JP2703474A JPS5523820B2 (enrdf_load_stackoverflow) | 1973-03-09 | 1974-03-08 | |
| CA194,467A CA1050023A (en) | 1973-03-09 | 1974-03-08 | Process for the preparation of benzylamines |
| DK358876A DK358876A (da) | 1973-07-28 | 1976-08-09 | Fremgangsmade til fremstilling af benzylaminer |
| NO773303A NO773303L (no) | 1973-07-28 | 1977-09-27 | Fremgangsm}te for fremstilling av benzylaminer |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2311637A DE2311637C3 (de) | 1973-03-09 | 1973-03-09 | Verfahren zur Herstellung von 2-Aminobenzylaminen |
| DE19732338408 DE2338408C3 (de) | 1973-07-28 | Verfahren zur Herstellung von 2-Amino-benzylaminen | |
| DE19732338409 DE2338409A1 (de) | 1973-03-09 | 1973-07-28 | Neues verfahren zur herstellung von 2-acylamino-benzylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2338409A1 true DE2338409A1 (de) | 1975-02-13 |
Family
ID=27185122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732338409 Pending DE2338409A1 (de) | 1973-03-09 | 1973-07-28 | Neues verfahren zur herstellung von 2-acylamino-benzylaminen |
Country Status (14)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53114748U (enrdf_load_stackoverflow) * | 1977-02-21 | 1978-09-12 | ||
| CN102924295B (zh) * | 2012-10-09 | 2014-10-29 | 石家庄东方药业有限公司 | 一种盐酸溴己新晶体及其制备方法和用途 |
| CN103145564B (zh) * | 2013-03-15 | 2014-06-18 | 湖北美林药业有限公司 | 盐酸溴己新化合物及其药物组合物 |
-
1973
- 1973-07-28 DE DE19732338409 patent/DE2338409A1/de active Pending
-
1974
- 1974-01-29 AT AT68274*#A patent/AT329020B/de not_active IP Right Cessation
- 1974-02-05 FI FI316/74A patent/FI60550C/fi active
- 1974-02-12 NL NL7401880A patent/NL7401880A/xx unknown
- 1974-02-19 BG BG025828A patent/BG21852A3/xx unknown
- 1974-02-19 ES ES423393A patent/ES423393A1/es not_active Expired
- 1974-03-06 CH CH317874A patent/CH605617A5/de not_active IP Right Cessation
- 1974-03-06 SU SU2003605A patent/SU512697A3/ru active
- 1974-03-06 CS CS7400001636A patent/CS180004B2/cs unknown
- 1974-03-07 HU HUTO956A patent/HU167188B/hu unknown
- 1974-03-08 JP JP2703474A patent/JPS5523820B2/ja not_active Expired
- 1974-03-08 SE SE7403159A patent/SE434942B/xx not_active IP Right Cessation
- 1974-03-08 CA CA194,467A patent/CA1050023A/en not_active Expired
- 1974-03-08 NO NO740820A patent/NO138406C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI60550B (fi) | 1981-10-30 |
| FI60550C (fi) | 1982-02-10 |
| ATA68274A (de) | 1975-07-15 |
| NO740820L (no) | 1974-09-10 |
| AT329020B (de) | 1976-04-26 |
| CS180004B2 (en) | 1977-12-30 |
| SE434942B (sv) | 1984-08-27 |
| HU167188B (enrdf_load_stackoverflow) | 1975-08-28 |
| JPS5523820B2 (enrdf_load_stackoverflow) | 1980-06-25 |
| SU512697A3 (ru) | 1976-04-30 |
| CA1050023A (en) | 1979-03-06 |
| ES423393A1 (es) | 1976-05-16 |
| JPS505338A (enrdf_load_stackoverflow) | 1975-01-21 |
| NO138406C (no) | 1978-08-30 |
| DE2338408A1 (de) | 1975-03-13 |
| DE2338408B2 (de) | 1976-05-20 |
| NL7401880A (enrdf_load_stackoverflow) | 1974-09-11 |
| NO138406B (no) | 1978-05-22 |
| BG21852A3 (bg) | 1976-09-20 |
| CH605617A5 (en) | 1978-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |