PL70934B1 - - Google Patents
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- Publication number
- PL70934B1 PL70934B1 PL1971152173A PL15217371A PL70934B1 PL 70934 B1 PL70934 B1 PL 70934B1 PL 1971152173 A PL1971152173 A PL 1971152173A PL 15217371 A PL15217371 A PL 15217371A PL 70934 B1 PL70934 B1 PL 70934B1
- Authority
- PL
- Poland
- Prior art keywords
- pka
- reactions
- organic
- solvent
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000007530 organic bases Chemical class 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- 150000002118 epoxides Chemical class 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003637 steroidlike Effects 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000003945 chlorohydrins Chemical class 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
- HNNIWKQLJSNAEQ-UHFFFAOYSA-N Benzydamine hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 HNNIWKQLJSNAEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ROFVJSWBDQUQGW-UHFFFAOYSA-N piperidin-1-ium;bromide Chemical compound Br.C1CCNCC1 ROFVJSWBDQUQGW-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI415A HU164657B (en:Method) | 1970-12-16 | 1970-12-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL70934B1 true PL70934B1 (en:Method) | 1974-04-30 |
Family
ID=11000855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971152173A PL70934B1 (en:Method) | 1970-12-16 | 1971-12-15 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT323905B (en:Method) |
| CA (1) | CA932718A (en:Method) |
| CS (1) | CS163263B2 (en:Method) |
| ES (1) | ES397796A1 (en:Method) |
| FR (1) | FR2118534A5 (en:Method) |
| HU (1) | HU164657B (en:Method) |
| NL (1) | NL166478C (en:Method) |
| PL (1) | PL70934B1 (en:Method) |
| SE (1) | SE377571B (en:Method) |
| SU (1) | SU413674A3 (en:Method) |
| YU (1) | YU35151B (en:Method) |
-
1970
- 1970-12-16 HU HURI415A patent/HU164657B/hu unknown
-
1971
- 1971-12-07 CA CA129512A patent/CA932718A/en not_active Expired
- 1971-12-09 ES ES397796A patent/ES397796A1/es not_active Expired
- 1971-12-09 YU YU3081/71A patent/YU35151B/xx unknown
- 1971-12-13 FR FR7144642A patent/FR2118534A5/fr not_active Expired
- 1971-12-13 AT AT1066771A patent/AT323905B/de not_active IP Right Cessation
- 1971-12-14 SE SE7116024A patent/SE377571B/xx unknown
- 1971-12-15 NL NL7117203.A patent/NL166478C/xx not_active IP Right Cessation
- 1971-12-15 SU SU1725130A patent/SU413674A3/ru active
- 1971-12-15 CS CS8712A patent/CS163263B2/cs unknown
- 1971-12-15 PL PL1971152173A patent/PL70934B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA932718A (en) | 1973-08-28 |
| SU413674A3 (en:Method) | 1974-01-30 |
| ES397796A1 (es) | 1974-05-16 |
| HU164657B (en:Method) | 1974-03-28 |
| DE2162569A1 (de) | 1972-07-13 |
| NL166478C (nl) | 1981-08-17 |
| FR2118534A5 (en) | 1972-07-28 |
| YU35151B (en) | 1980-09-25 |
| NL7117203A (en:Method) | 1972-06-20 |
| CS163263B2 (en:Method) | 1975-08-29 |
| AT323905B (de) | 1975-08-11 |
| NL166478B (nl) | 1981-03-16 |
| SE377571B (en:Method) | 1975-07-14 |
| YU308171A (en) | 1980-03-15 |
| DE2162569B2 (de) | 1977-01-27 |
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