RO95239B1 - Process for preparing the n-(1-cyclohexanyl-methyl-2-pyrrolidinylmethyl)-8-ethyl- sulphonyl-1,5-benzodioxepan-6-carboxamide - Google Patents
Process for preparing the n-(1-cyclohexanyl-methyl-2-pyrrolidinylmethyl)-8-ethyl- sulphonyl-1,5-benzodioxepan-6-carboxamideInfo
- Publication number
- RO95239B1 RO95239B1 RO124499A RO12449986A RO95239B1 RO 95239 B1 RO95239 B1 RO 95239B1 RO 124499 A RO124499 A RO 124499A RO 12449986 A RO12449986 A RO 12449986A RO 95239 B1 RO95239 B1 RO 95239B1
- Authority
- RO
- Romania
- Prior art keywords
- benzodioxepan
- pyrrolidinylmethyl
- carboxamide
- ethylsulfonyl
- carboxylic acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- XUXFXVMZIJMUIO-UHFFFAOYSA-N 3,4-dihydro-2h-1,5-benzodioxepine-6-carboxylic acid Chemical compound O1CCCOC2=C1C=CC=C2C(=O)O XUXFXVMZIJMUIO-UHFFFAOYSA-N 0.000 abstract 1
- -1 8-ethylsulfonyl-1,5-benzodioxane-6-carboxylic acid chloride Chemical compound 0.000 abstract 1
- BYNWKEUOAHFYLS-UHFFFAOYSA-N 8-ethylsulfonyl-3,4-dihydro-2h-1,5-benzodioxepine-6-carboxylic acid Chemical compound O1CCCOC2=C1C=C(S(=O)(=O)CC)C=C2C(O)=O BYNWKEUOAHFYLS-UHFFFAOYSA-N 0.000 abstract 1
- PUVRPONDSAVLJE-UHFFFAOYSA-N [1-(cyclohexen-1-ylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1=CCCCC1 PUVRPONDSAVLJE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea N-(1-ciclohexenilmetil-2- pirolidinilmetil-8-etilsulfonil-1,5-benzodioxepan-6-carboxamidei cu formula I (vezi formula în pag. 1 a descrierii), caracterizat prin aceea ca acidul 1,5-benzodioxepan-6-carboxilic se trateaza cu acid clorsulfonic la temperatura camerei, cu formarea acidului 8-etilsulfonil-1,5- benzodioxepan-6-carboxilic, care, prin tratare cu bicarbonat de sodiu si sulfit de sodiu, la 70...80 degree C, urmata de refluxare cu iodura de etil, în prezenta de etanol ca solvent si hidroxid de sodiu ca acid bazic, duce la formarea clorurii acidului 8-etilsulfonil-1,5-benzodioxepan-6- carboxilic, care se condenseaza cu 1-(1-ciclohexenilmetil)-2-aminometilpirolidina.The invention relates to a process for the preparation of N- (1-cyclohexenylmethyl-2-pyrrolidinylmethyl-8-ethylsulfonyl-1,5-benzodioxepane-6-carboxamide of the formula I (see formula on page 1 of the description) 1,5-benzodioxepan-6-carboxylic acid is treated with chlorosulfonic acid at room temperature to form 8-ethylsulfonyl-1,5-benzodioxepan-6-carboxylic acid, which, by treatment with sodium bicarbonate and sodium sulfite, at 70 DEG-80 DEG C., followed by refluxing with ethyl iodide, in the presence of ethanol as the solvent and sodium hydroxide as the base acid, leads to the formation of 8-ethylsulfonyl-1,5-benzodioxane-6-carboxylic acid chloride, which is condensed with 1- (1-cyclohexenylmethyl) -2-aminomethylpyrrolidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO124499A RO95239B1 (en) | 1986-08-11 | 1986-08-11 | Process for preparing the n-(1-cyclohexanyl-methyl-2-pyrrolidinylmethyl)-8-ethyl- sulphonyl-1,5-benzodioxepan-6-carboxamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RO124499A RO95239B1 (en) | 1986-08-11 | 1986-08-11 | Process for preparing the n-(1-cyclohexanyl-methyl-2-pyrrolidinylmethyl)-8-ethyl- sulphonyl-1,5-benzodioxepan-6-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RO95239B1 true RO95239B1 (en) | 1988-09-16 |
Family
ID=40904664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO124499A RO95239B1 (en) | 1986-08-11 | 1986-08-11 | Process for preparing the n-(1-cyclohexanyl-methyl-2-pyrrolidinylmethyl)-8-ethyl- sulphonyl-1,5-benzodioxepan-6-carboxamide |
Country Status (1)
| Country | Link |
|---|---|
| RO (1) | RO95239B1 (en) |
-
1986
- 1986-08-11 RO RO124499A patent/RO95239B1/en unknown
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