GB778936A - Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls - Google Patents
Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzylsInfo
- Publication number
- GB778936A GB778936A GB26972/55A GB2697255A GB778936A GB 778936 A GB778936 A GB 778936A GB 26972/55 A GB26972/55 A GB 26972/55A GB 2697255 A GB2697255 A GB 2697255A GB 778936 A GB778936 A GB 778936A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iminodibenzyl
- dimethylaminopropyl
- dichloro
- hydrochloride
- alkylene
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 dimethyl-iminodibenzyl Chemical group 0.000 abstract 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 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
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001447 alkali salts Chemical class 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 239000001177 diphosphate Substances 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 1
- 235000011180 diphosphates Nutrition 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical class [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0778936/IV(b)/1> wherein the alkylene radical has 2 to 6 carbon atoms and 2 to 4 bridging members, Am represents a dialkylamino radical with alkyl radicals having 1 to 3 carbon atoms or an alkylene imino radical with 5 or 6 ring members and X represents a halogen atom or a methyl group. Such compounds are obtained by reacting the appropriate substituted iminodibenzyl with a reactive ester of an alcohol of the general formula HO-alkylene-Am, and the products are if desired converted into their quaternary ammonium compounds or into their salts by treatment with halides or sulphates of aliphatic or araliphatic alcohols or with inorganic or organic acids. The dihalogeno- or dimethyl-iminodibenzyl is advantageously converted into its alkali salt by reaction with sodium, lithium or potassium amides or sodium or potassium metals. Iminodibenzyls having 3.7- or 1.9-dibromo, 2.8-, 3.7- or 1.9-dichloro or 3.7- or 2.8-dimethyl substituents are specified. They can be obtained by heating the corresponding substituted diamino-dibenzyls as diphosphates or in the presence of polyphosphoric acid. Salts mentioned are those with hydrochloric, hydrobromic, sulphuric, phosphoric, methane sulphonic, ethane disulphonic, acetic, citric, malic, succinic, tartaric, benzoic and phthalic acids. Examples describe the preparation of (1) 5-(b -dimethylaminopropyl) - 3.7 - dichloro - iminodibenzyl and its hydrochloride; (2) 5-(g -dimethylaminopropyl) - 3.7 - dichloroiminodibenzyl and its hydrochloride; 5-(b -piperidinoethyl)-3.7-dichloro-iminodibenzyl and its hydrochloride; 5 - (g - dimethylaminopropyl)-2.8 - dimethyliminodibenzyl; 5 - (b - pyrrolidinoethyl) - 3.7 - dibromo - iminodibenzyl. Specification 777,546 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH778936X | 1954-09-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB778936A true GB778936A (en) | 1957-07-17 |
Family
ID=4536036
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26972/55A Expired GB778936A (en) | 1954-09-22 | 1955-09-21 | Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB778936A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108409660A (en) * | 2018-05-14 | 2018-08-17 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers |
CN108409659A (en) * | 2018-05-14 | 2018-08-17 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers key intermediate |
CN108707112A (en) * | 2018-05-14 | 2018-10-26 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers chlorine nitre phenyl intermediates |
-
1955
- 1955-09-21 GB GB26972/55A patent/GB778936A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108409660A (en) * | 2018-05-14 | 2018-08-17 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers |
CN108409659A (en) * | 2018-05-14 | 2018-08-17 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers key intermediate |
CN108707112A (en) * | 2018-05-14 | 2018-10-26 | 刘可 | A kind of preparation method of antidepressant agents impurity isomers chlorine nitre phenyl intermediates |
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