CA1050541A - Process for the preparation of benzylamines - Google Patents
Process for the preparation of benzylaminesInfo
- Publication number
- CA1050541A CA1050541A CA208,639A CA208639A CA1050541A CA 1050541 A CA1050541 A CA 1050541A CA 208639 A CA208639 A CA 208639A CA 1050541 A CA1050541 A CA 1050541A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- group
- compound
- benzyl
- formula
- 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 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000003939 benzylamines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- -1 benzylpyridinium compound Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 claims description 3
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 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
- 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 3
- KSNNEUZOAFRTDS-UHFFFAOYSA-N fominoben Chemical compound ClC=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1CN(C)CC(=O)N1CCOCC1 KSNNEUZOAFRTDS-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
- JGRVPGDTWHHRAL-UHFFFAOYSA-M [Br-].NC1=C(C[N+]2=CC=CC=C2)C=C(C=C1Br)Br Chemical compound [Br-].NC1=C(C[N+]2=CC=CC=C2)C=C(C=C1Br)Br JGRVPGDTWHHRAL-UHFFFAOYSA-M 0.000 claims 2
- DYJSUCXNMLSPHE-UHFFFAOYSA-M [I-].NC1=C(C[N+](C)(C)C)C=C(C=C1Br)Br Chemical compound [I-].NC1=C(C[N+](C)(C)C)C=C(C=C1Br)Br DYJSUCXNMLSPHE-UHFFFAOYSA-M 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- KXBUUYBPURYTRE-UHFFFAOYSA-N N-[3-chloro-2-(pyridin-1-ium-1-ylmethyl)phenyl]benzamide bromide Chemical compound [Br-].C(C1=CC=CC=C1)(=O)NC1=C(C[N+]2=CC=CC=C2)C(=CC=C1)Cl KXBUUYBPURYTRE-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- UZZSSTXYFRORNI-UHFFFAOYSA-N n-[2-(aminomethyl)phenyl]benzamide Chemical class NCC1=CC=CC=C1NC(=O)C1=CC=CC=C1 UZZSSTXYFRORNI-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- 230000001766 physiological effect Effects 0.000 abstract description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 abstract description 2
- 230000004936 stimulating effect Effects 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OPDNNNDSAIGDQM-UHFFFAOYSA-N (2-benzamido-6-chlorophenyl)methyl-trimethylazanium bromide Chemical compound [Br-].C(C1=CC=CC=C1)(=O)NC1=C(C[N+](C)(C)C)C(=CC=C1)Cl OPDNNNDSAIGDQM-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HKGOUZYFCRROHG-UHFFFAOYSA-N N-[3-bromo-2-(pyridin-1-ium-1-ylmethyl)phenyl]benzamide bromide Chemical compound [Br-].C(C1=CC=CC=C1)(=O)NC1=C(C[N+]2=CC=CC=C2)C(=CC=C1)Br HKGOUZYFCRROHG-UHFFFAOYSA-N 0.000 description 1
- NRXQKDWVBRAEBM-UHFFFAOYSA-N N-[3-bromo-2-[[methyl-(2-morpholin-4-yl-2-oxoethyl)amino]methyl]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=C(CN(CC(=O)N2CCOCC2)C)C(=CC=C1)Br NRXQKDWVBRAEBM-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 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)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742402577 DE2402577C3 (de) | 1974-01-19 | Verfahren zur Herstellung von Benzylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050541A true CA1050541A (en) | 1979-03-13 |
Family
ID=5905201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA208,639A Expired CA1050541A (en) | 1974-01-19 | 1974-09-06 | Process for the preparation of benzylamines |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS50101329A (en, 2012) |
| AT (1) | AT327876B (en, 2012) |
| BG (1) | BG22385A4 (en, 2012) |
| CA (1) | CA1050541A (en, 2012) |
| CH (1) | CH612663A5 (en, 2012) |
| CS (1) | CS167213B2 (en, 2012) |
| DK (1) | DK473174A (en, 2012) |
| ES (1) | ES429772A2 (en, 2012) |
| FI (1) | FI60552C (en, 2012) |
| HU (1) | HU167562B (en, 2012) |
| NL (1) | NL7410822A (en, 2012) |
| PL (1) | PL91730B1 (en, 2012) |
| SE (1) | SE439157B (en, 2012) |
| YU (1) | YU37110B (en, 2012) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT332375B (de) * | 1973-04-13 | 1976-09-27 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen aminobenzylaminen sowie deren saureadditionssalzen |
-
1974
- 1974-08-08 HU HUBO1513A patent/HU167562B/hu unknown
- 1974-08-08 AT AT651074A patent/AT327876B/de active
- 1974-08-13 NL NL7410822A patent/NL7410822A/xx not_active Application Discontinuation
- 1974-08-22 FI FI2471/74A patent/FI60552C/fi active
- 1974-09-05 ES ES429772A patent/ES429772A2/es not_active Expired
- 1974-09-05 YU YU2393/74A patent/YU37110B/xx unknown
- 1974-09-06 SE SE7411314A patent/SE439157B/xx not_active IP Right Cessation
- 1974-09-06 CH CH1218874A patent/CH612663A5/xx not_active IP Right Cessation
- 1974-09-06 DK DK473174A patent/DK473174A/da not_active Application Discontinuation
- 1974-09-06 JP JP49102861A patent/JPS50101329A/ja active Pending
- 1974-09-06 CA CA208,639A patent/CA1050541A/en not_active Expired
- 1974-09-07 BG BG027656A patent/BG22385A4/xx unknown
- 1974-09-07 PL PL1974173959A patent/PL91730B1/pl unknown
- 1974-09-13 CS CS6313A patent/CS167213B2/cs unknown
-
1977
- 1977-06-29 JP JP7769277A patent/JPS5353624A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AT327876B (de) | 1976-02-25 |
| DK473174A (en, 2012) | 1975-09-08 |
| JPS50101329A (en, 2012) | 1975-08-11 |
| CH612663A5 (en) | 1979-08-15 |
| DE2402577B2 (de) | 1976-09-02 |
| NL7410822A (nl) | 1975-07-22 |
| ATA651074A (de) | 1975-05-15 |
| DE2402577A1 (de) | 1975-12-18 |
| YU239374A (en) | 1983-04-27 |
| FI60552B (fi) | 1981-10-30 |
| ES429772A2 (es) | 1977-03-16 |
| SE7411314L (en, 2012) | 1975-07-21 |
| FI247174A7 (en, 2012) | 1975-07-20 |
| BG22385A4 (bg) | 1977-02-20 |
| JPS568022B2 (en, 2012) | 1981-02-20 |
| HU167562B (en, 2012) | 1975-11-28 |
| YU37110B (en) | 1984-08-31 |
| SE439157B (sv) | 1985-06-03 |
| JPS5353624A (en) | 1978-05-16 |
| CS167213B2 (en, 2012) | 1976-04-29 |
| PL91730B1 (en, 2012) | 1977-03-31 |
| FI60552C (fi) | 1982-02-10 |
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