GB825561A - Phenothiazine derivatives and process for their preparation - Google Patents
Phenothiazine derivatives and process for their preparationInfo
- Publication number
- GB825561A GB825561A GB21601/56A GB2160156A GB825561A GB 825561 A GB825561 A GB 825561A GB 21601/56 A GB21601/56 A GB 21601/56A GB 2160156 A GB2160156 A GB 2160156A GB 825561 A GB825561 A GB 825561A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenthiazine
- pyrrolidyl
- spiro
- cyclohexane
- chloro
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises phenthiazines of the formula <FORM:0825561/IV (b)/1> (wherein Z is hydrogen, halogen, or alkyl or alkoxy groups containing a maximum of eight carbon atoms, R1 and R11 are hydrogen or methyl, m is one or two, n is an integer from 2 to 6 inclusive and -CnH2nis alkylene such that at least two carbon atoms link the nitrogen atoms) co-ordination complexes such as the corresponding sulphoxides, sulphoxide-amine oxides, quaternary ammonium derivatives and acid addition salts of the free base or its coordination complexes, together with processes for their preparation by reacting 2-spiro-substituted pyrrolidyl-alkyl halides and 2-spirosubstituted pyrrolidines with 10-unsubstituted phenthiazines and 10-(o -halo-alkyl)-phenthiazines respectively in an inert medium in the presence of an alkaline condensing agent, e.g. alkali metal hydroxides, amides, hydrides or alkoxides, and preferably under nitrogen or other inert gas. Specified acid addition salts are hydrochloride, hydrobromide, hydroiodide, sulphate, citrate, acetate, succinate, nitrate, and phosphate, and quaternary derivatives may be derived from methyl bromide and iodide, ethyl and benzyl chloride and allyl bromide. The sulphoxide and sulphoxide-amine oxides are prepared by oxidation of the corresponding phenthiazine compounds with a peracid or hydrogen peroxide. Specified starting materials include 1- and 3-fluoro-, 2-, 3- and 4-chloro-, 2-bromo-, 3-methoxy- and 4-methyl-phenthiazine, and 4-chloro-, 2-methyl-, 2-chloro-, and 4-iso-butyl-10-(b -chloroethyl)-phen-thiazine, 10-(b -chloroethyl)-, 3-ethoxy-10-(g -chloropropyl)- and 2-chloro-10-(b -chloropropyl)-phenthiazine. In examples: (1) phenthiazine and sodamide are refluxed in toluene, treated with b -(spiro-[cyclohexane-1,21-pyrrolidyl-11])-pyrrolidyl - 11] - ethyl) - phenthiazine hydro-chloride hydrate, and subsequently the free base; (2) 2-chlorophenothiazine (Chemical Abstracts numbering) and sodamide are refluxed in toluene and then with g -(spiro-[cyclohexane-1,21 - pyrrolidyl - 11]) - propyl chloride, the mixture extracted with ether and extracts treated with dilute HCl giving 2-chloro-10-(g -spiro-[cyclohexane-1, 21-pyrrolidyl-11]-propyl)-phenthiazine hydrochloride, and subsequently the free base on treatment with NaOH. Other compounds similarly obtained are 10-(b -spiro[cyclohexane - 1,21 - pyrrolidyl - 11] - propyl) - phenthiazine, 10 - (b - spiro - [cyclopentane - 1,21 - pyrrolidyl - 11] - ethyl) - phenthiazine hydrochloride, 3 - methoxy - 10 - (b - spiro - [cyclohexane - 1,21 - pyrrolidyl - 11] - ethyl) - phenthiazine hydrochloride and 2-bromo-10-(g - spiro - [cyclohexane - 1,21 - pyrrolidyl - 11] - propyl)-phenthiazine. Specifications 716,206, 825,562 and 825,564 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US825561XA | 1955-07-18 | 1955-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB825561A true GB825561A (en) | 1959-12-16 |
Family
ID=22171928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21601/56A Expired GB825561A (en) | 1955-07-18 | 1956-07-12 | Phenothiazine derivatives and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB825561A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349246A (en) * | 2020-02-17 | 2020-06-30 | 山东师范大学 | Metal organic framework for nitrogen adsorption and/or storage and application thereof |
-
1956
- 1956-07-12 GB GB21601/56A patent/GB825561A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349246A (en) * | 2020-02-17 | 2020-06-30 | 山东师范大学 | Metal organic framework for nitrogen adsorption and/or storage and application thereof |
| CN111349246B (en) * | 2020-02-17 | 2021-11-09 | 山东师范大学 | Metal organic framework for nitrogen adsorption and/or storage and application thereof |
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