GB914718A - Substituted 5-h-dibenz[b,f]azepines and their preparation - Google Patents
Substituted 5-h-dibenz[b,f]azepines and their preparationInfo
- Publication number
- GB914718A GB914718A GB678061A GB678061A GB914718A GB 914718 A GB914718 A GB 914718A GB 678061 A GB678061 A GB 678061A GB 678061 A GB678061 A GB 678061A GB 914718 A GB914718 A GB 914718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- reaction
- pict
- chloride
- hexamethylenimine
- 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
- 150000001538 azepines Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 6
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 229940058015 1,3-butylene glycol Drugs 0.000 abstract 1
- UDSOIUSFQZZUPF-UHFFFAOYSA-N 3-chlorobutyl acetate Chemical compound CC(Cl)CCOC(C)=O UDSOIUSFQZZUPF-UHFFFAOYSA-N 0.000 abstract 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- OSNDUYDDOHEKEE-UHFFFAOYSA-N azepane-2,7-dione Chemical compound O=C1CCCCC(=O)N1 OSNDUYDDOHEKEE-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- -1 halogen alkane carboxylic acid halides Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises 5H-dibenz[b,f]azepines of general formula <PICT:0914718/IV (b)/1> wherein X represents -CH2.CH2-, Y1 and Y2 each represent hydrogen, halogen, or an alkyl group of at most three carbon atoms, Z represents a straight or branched alkylene chain of at most six carbon atoms, and Am represents a hexamethylenimine radical which may be substituted with one or more alkyl radicals having at most 3 carbon atoms, their acidaddition and quaternary ammonium salts, and their preparation by (1) reaction of a compound of general formula <PICT:0914718/IV (b)/2> in the presence of a condensing agent with a reactive ester of an aminoalcohol of general formula HO-Z-Am (III) (2) thermal decarboxylation of a compound of general formula <PICT:0914718/IV (b)/3> (3) reaction of a reactive ester of a compound of general formula <PICT:0914718/IV (b)/4> with an amine of general formula Am-H (VI) or (4) by treating a compound of general formula <PICT:0914718/IV (b)/5> wherein Z1 and Am1 represent radicals that correspond to Z and Am respectively except that in at least one of them there is at least one carbonyl group instead of a methylene group bound to a nitrogen atom, with an alkali metal-earth hydride. The products are useful as pharmaceutical agents. Esters of general formula (IV) are obtained by reaction of phosgene with heterocycles of general formula (II), and reaction of the 5-chlorocarbonyliminodibenzyls so obtained with aminoalcohols of general formula (III). g -Hexamethyleniminopropanol is prepared by reduction of g -hexamethyleniminopropionic acid ethyl ester with lithium aluminium hydride. Hexamethylenimines of general formula (VI) are prepared by reduction of the corresponding e -caprolactams with lithium aluminium hydride. g -Hexamethylenimino-n-butyl chloride is obtained from 1,3-butylene glycol by reaction with acetyl chloride to form 3-chloro-n-butyl acetate, reaction of the latter with hexamethylenimine and conversion of the g -hexamethyleniminobutanol formed into the chloride, and g -hexamethylenimino-b -methylpropyl chloride is obtained by adding hydrogen bromide to b -methallyl chloride in the presence p of dibenzoyl peroxide and reacting the g -bromo-b -methylpropyl chloride formed with hexamethylenimine. 5-(a -Tert-aminocarbonylalkyl)iminodibenzyls are obtained by reaction of alkali metal derivatives of iminodibenzyls of general formula (II) with low a -bromoalkane carboxylic acid N,Nhexamethylene amides. 5-Hexamethyleniminoalkanoyliminodibenzyls are obtained by reacting alkali metal derivatives of compounds of general formula (II) with halogen alkane carboxylic acid halides and then reacting the halogen alkanoyl compounds obtained with a hexamethylenimine of general formula (VI). Other intermediates of general formula (VII) are obtained by reaction of esters of compounds of general formula (V) with alkali metal compounds of e -caprolactam or adipimide. Specifications 912,013 and 914,717 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215360 | 1960-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB914718A true GB914718A (en) | 1963-01-02 |
Family
ID=4227106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB678061A Expired GB914718A (en) | 1960-02-26 | 1961-02-24 | Substituted 5-h-dibenz[b,f]azepines and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE600611A (en) |
| ES (3) | ES265234A1 (en) |
| GB (1) | GB914718A (en) |
-
1961
- 1961-02-24 BE BE600611A patent/BE600611A/en unknown
- 1961-02-24 GB GB678061A patent/GB914718A/en not_active Expired
- 1961-02-25 ES ES0265234A patent/ES265234A1/en not_active Expired
- 1961-02-25 ES ES0265236A patent/ES265236A1/en not_active Expired
- 1961-02-25 ES ES0265235A patent/ES265235A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES265236A1 (en) | 1961-08-16 |
| BE600611A (en) | 1961-08-24 |
| ES265235A1 (en) | 1961-08-16 |
| ES265234A1 (en) | 1961-08-16 |
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