IL38256A - Process for the preparation of 10-amino-10,11-dihydro-dibenzo(b,f)azepines and intermediates for use therein - Google Patents
Process for the preparation of 10-amino-10,11-dihydro-dibenzo(b,f)azepines and intermediates for use thereinInfo
- Publication number
- IL38256A IL38256A IL38256A IL3825671A IL38256A IL 38256 A IL38256 A IL 38256A IL 38256 A IL38256 A IL 38256A IL 3825671 A IL3825671 A IL 3825671A IL 38256 A IL38256 A IL 38256A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- formula
- process according
- dibenzo
- aminoborane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 6
- JQOTXDOJGISJCB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepin-5-amine Chemical class NC1CC2=CC=CC=C2NC2=CC=CC=C12 JQOTXDOJGISJCB-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- HUQOFZLCQISTTJ-UHFFFAOYSA-N diethylaminoboron Chemical compound CCN([B])CC HUQOFZLCQISTTJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- YPTUAQWMBNZZRN-UHFFFAOYSA-N dimethylaminoboron Chemical group [B]N(C)C YPTUAQWMBNZZRN-UHFFFAOYSA-N 0.000 claims description 2
- TVJORGWKNPGCDW-UHFFFAOYSA-N aminoboron Chemical group N[B] TVJORGWKNPGCDW-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 238000005576 amination reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- QXJIABOUHLYVHP-UHFFFAOYSA-N n-chloromethanamine Chemical compound CNCl QXJIABOUHLYVHP-UHFFFAOYSA-N 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- NDZUMKRLIPIEQP-UHFFFAOYSA-N 4,10-dihydroxyperylene-3,9-dione Chemical compound C1=CC2=C(C=CC3=O)C4C3=C(O)C=CC4C(C=CC3=O)=C2C3=C1O NDZUMKRLIPIEQP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KKAXNAVSOBXHTE-UHFFFAOYSA-N boranamine Chemical class NB KKAXNAVSOBXHTE-UHFFFAOYSA-N 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000003179 convulsant agent Substances 0.000 description 1
- 230000003226 decolorizating effect Effects 0.000 description 1
- 150000007655 dibenzoazepines Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7043177A FR2116251B1 (de) | 1970-12-01 | 1970-12-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38256A0 IL38256A0 (en) | 1972-01-27 |
| IL38256A true IL38256A (en) | 1974-12-31 |
Family
ID=9065025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38256A IL38256A (en) | 1970-12-01 | 1971-11-30 | Process for the preparation of 10-amino-10,11-dihydro-dibenzo(b,f)azepines and intermediates for use therein |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5729465B1 (de) |
| AT (1) | AT313283B (de) |
| BE (1) | BE776057A (de) |
| CH (1) | CH542211A (de) |
| DE (1) | DE2159678C3 (de) |
| FR (1) | FR2116251B1 (de) |
| GB (1) | GB1323219A (de) |
| HU (1) | HU162858B (de) |
| IL (1) | IL38256A (de) |
| IT (1) | IT1019519B (de) |
| NL (1) | NL7116100A (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2881398A1 (de) | 2013-12-04 | 2015-06-10 | Université de Bordeaux I | Verfahren zur Herstellung von Aminoarylboranverbindungen oder Derivaten davon |
| CN110372633B (zh) * | 2019-08-01 | 2022-11-04 | 台州学院 | 一种催化亚氨基二苄碳基衍生物还原的方法 |
-
1970
- 1970-12-01 FR FR7043177A patent/FR2116251B1/fr not_active Expired
-
1971
- 1971-11-23 NL NL7116100A patent/NL7116100A/xx active Search and Examination
- 1971-11-29 HU HURO634A patent/HU162858B/hu unknown
- 1971-11-29 JP JP9538971A patent/JPS5729465B1/ja active Pending
- 1971-11-30 BE BE776057A patent/BE776057A/xx unknown
- 1971-11-30 IL IL38256A patent/IL38256A/en unknown
- 1971-11-30 CH CH1742071A patent/CH542211A/fr not_active IP Right Cessation
- 1971-12-01 DE DE2159678A patent/DE2159678C3/de not_active Expired
- 1971-12-01 AT AT1033271A patent/AT313283B/de not_active IP Right Cessation
- 1971-12-01 IT IT31909/71A patent/IT1019519B/it active
- 1971-12-01 GB GB5583771A patent/GB1323219A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL38256A0 (en) | 1972-01-27 |
| IT1019519B (it) | 1977-11-30 |
| DE2159678A1 (de) | 1972-06-22 |
| JPS5729465B1 (de) | 1982-06-23 |
| BE776057A (fr) | 1972-05-30 |
| AT313283B (de) | 1974-02-11 |
| FR2116251B1 (de) | 1974-03-22 |
| CH542211A (fr) | 1973-09-30 |
| HU162858B (de) | 1973-04-28 |
| FR2116251A1 (de) | 1972-07-13 |
| DE2159678B2 (de) | 1979-08-02 |
| NL7116100A (de) | 1972-06-05 |
| GB1323219A (en) | 1973-07-11 |
| DE2159678C3 (de) | 1980-03-27 |
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