GB939270A - A process for the production of 3-halo-iminodibenzyls - Google Patents
A process for the production of 3-halo-iminodibenzylsInfo
- Publication number
- GB939270A GB939270A GB4020660A GB4020660A GB939270A GB 939270 A GB939270 A GB 939270A GB 4020660 A GB4020660 A GB 4020660A GB 4020660 A GB4020660 A GB 4020660A GB 939270 A GB939270 A GB 939270A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iminodibenzyl
- formula
- compounds
- chloro
- chlorine
- 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
- 150000001875 compounds Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- NMZOSOMVILZBJL-UHFFFAOYSA-N 1-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=C(Cl)C=C2N(C(=O)C)C2=CC=CC=C21 NMZOSOMVILZBJL-UHFFFAOYSA-N 0.000 abstract 1
- QBSUAHGUFKVVTM-UHFFFAOYSA-N 1-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethanone Chemical group C1CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 QBSUAHGUFKVVTM-UHFFFAOYSA-N 0.000 abstract 1
- MHUXTOYYIDFXRF-UHFFFAOYSA-N 2-chloro-6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC(Cl)=CC=C21 MHUXTOYYIDFXRF-UHFFFAOYSA-N 0.000 abstract 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- -1 dialkylaminoalkyl halides Chemical class 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Compounds of the formula <FORM:0939270/IV(a)/1> where X is chlorine or bromine, are prepared by treating a compound of formula <FORM:0939270/IV(a)/2> with hydrogen at normal pressure and room temperature in the presence of a noble metal catalyst and a substantially equimolar amount of an inorganic or organic base, e.g. an alkali metal hydroxide or an amine. A preferred catalyst is palladium. In examples in which X is chlorine, iminodibenzyl is obtained as a by-product, and is isolated, after fractional distillation of the product, by crystallisation from methanol; or the desired fraction is reacted with acetyl chloride, the 5-acetyliminodibenzyl is separated from the 5-acetyl3-chloro-iminodibenzyl by fractional crystallisation, and the latter hydrolysed to 3-chloroiminodibenzyl. The compounds of formula I react with dialkylaminoalkyl halides to give medicinal compounds, such as 5-(g -dimethyl-aminopropyl)-3-chloro-iminodibenzyl. Specification 777,546 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8109659A CH375015A (en) | 1959-11-26 | 1959-11-26 | Process for the preparation of new N-heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB939270A true GB939270A (en) | 1963-10-09 |
Family
ID=4538498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4020660A Expired GB939270A (en) | 1959-11-26 | 1960-11-23 | A process for the production of 3-halo-iminodibenzyls |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE597485A (en) |
| CH (1) | CH375015A (en) |
| DE (1) | DE1178068B (en) |
| DK (1) | DK104677C (en) |
| ES (1) | ES262763A1 (en) |
| GB (1) | GB939270A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE83680T1 (en) * | 1988-10-25 | 1993-01-15 | Lego As | KIT WITH PLUG-IN BLOCKS FOR LAYER CONSTRUCTION. |
-
1959
- 1959-11-26 CH CH8109659A patent/CH375015A/en unknown
-
1960
- 1960-11-23 GB GB4020660A patent/GB939270A/en not_active Expired
- 1960-11-25 BE BE597485A patent/BE597485A/en unknown
- 1960-11-25 DK DK470460A patent/DK104677C/en active
- 1960-11-25 ES ES0262763A patent/ES262763A1/en not_active Expired
- 1960-11-25 DE DE1960G0031009 patent/DE1178068B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH375015A (en) | 1964-02-15 |
| BE597485A (en) | 1961-05-25 |
| ES262763A1 (en) | 1961-06-01 |
| DE1178068B (en) | 1964-09-17 |
| DK104677C (en) | 1966-06-20 |
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