FI60552C - Nytt foerfarande foer framstaellning av 2-amino-3,5-dibrom-benzylaminer - Google Patents
Nytt foerfarande foer framstaellning av 2-amino-3,5-dibrom-benzylaminer Download PDFInfo
- Publication number
- FI60552C FI60552C FI2471/74A FI247174A FI60552C FI 60552 C FI60552 C FI 60552C FI 2471/74 A FI2471/74 A FI 2471/74A FI 247174 A FI247174 A FI 247174A FI 60552 C FI60552 C FI 60552C
- Authority
- FI
- Finland
- Prior art keywords
- amino
- dibromo
- general formula
- benzylaminer
- dibrom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- -1 hydroxycyclohexyl group Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NAIJZCXBMHHHDM-UHFFFAOYSA-N 2-(aminomethyl)-4,6-dibromoaniline Chemical class NCC1=CC(Br)=CC(Br)=C1N NAIJZCXBMHHHDM-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000005210 alkyl ammonium group Chemical group 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-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
- 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 description 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 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 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 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase 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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QNVKOSLOVOTXKF-PFWPSKEQSA-N chembl1514634 Chemical compound Cl.NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 QNVKOSLOVOTXKF-PFWPSKEQSA-N 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
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 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
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742402577 DE2402577C3 (de) | 1974-01-19 | Verfahren zur Herstellung von Benzylaminen | |
| DE2402577 | 1974-01-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI247174A7 FI247174A7 (en, 2012) | 1975-07-20 |
| FI60552B FI60552B (fi) | 1981-10-30 |
| FI60552C true FI60552C (fi) | 1982-02-10 |
Family
ID=5905201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2471/74A FI60552C (fi) | 1974-01-19 | 1974-08-22 | Nytt foerfarande foer framstaellning av 2-amino-3,5-dibrom-benzylaminer |
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 |
| CA1050541A (en) | 1979-03-13 |
| 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 |
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