ES434650A2 - Method for the preparation of derivatives of spiro-(4,5)-decane and derivatives thus obtained - Google Patents
Method for the preparation of derivatives of spiro-(4,5)-decane and derivatives thus obtainedInfo
- Publication number
- ES434650A2 ES434650A2 ES434650A ES434650A ES434650A2 ES 434650 A2 ES434650 A2 ES 434650A2 ES 434650 A ES434650 A ES 434650A ES 434650 A ES434650 A ES 434650A ES 434650 A2 ES434650 A2 ES 434650A2
- Authority
- ES
- Spain
- Prior art keywords
- formula
- temperature
- adduct
- piperidone
- vii
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical class C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- -1 N-substituted 4-piperidone Chemical class 0.000 abstract 2
- 238000006969 Curtius rearrangement reaction Methods 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 230000000750 progressive effect Effects 0.000 abstract 1
- 239000011877 solvent mixture Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Improvements introduced in the object of the main patent nº 396186, granted on October 24, 1973, envelopes Procedure for the preparation of a chemical synthesis of oxa-1, oxo-2, diaza-3,8, phenethyl-8, spiro (4,5) decane, of general formula (I), starting from the N-substituted 4-piperidone of formula (IV), characterized in that the N-substituted 4-piperidone is reacted, according to the technique, of the modified Reformatzkij, in a solvent mixture of benzene and anhydrous ethyl ether, at a temperature between 0 and 15ºC, with the organometallic adduct of the formula: **(See formula)** derived from an alpha-halogen-ester (V), with precipitation, at low temperature, and by progressive addition of ether, from the adduct of formula: **(See formula)** This adduct is hydrolyzed with aqueous acetic acid to the betahydroxyester (VI), which is reacted for a time of 8-30 hours and at a temperature of 20-60C, with excess hydrazine NH2NH2H20, in the limits of 1: 1: 3, at 1: 100, obtaining the corresponding β-hydroxyhydride (VII), and finally the β-hydroxyhydrazides (VII) undergo a Curtius rearrangement reaction by the action of excess nitrous acid, in the presence of dilute mineral acid, at temperature Variable between room temperature and 60ºC keeping the acidic aqueous mixture under a layer of organic solvent. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205374A CH601304A5 (en) | 1974-02-12 | 1974-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES434650A2 true ES434650A2 (en) | 1977-02-01 |
Family
ID=4224819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES434650A Expired ES434650A2 (en) | 1974-02-12 | 1975-02-12 | Method for the preparation of derivatives of spiro-(4,5)-decane and derivatives thus obtained |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS50112376A (en) |
| AR (1) | AR207856A1 (en) |
| AU (1) | AU498871B2 (en) |
| BE (1) | BE825444R (en) |
| CA (1) | CA1033363A (en) |
| CH (1) | CH601304A5 (en) |
| DE (1) | DE2505143A1 (en) |
| ES (1) | ES434650A2 (en) |
| FR (1) | FR2262666A2 (en) |
| GB (1) | GB1495647A (en) |
| ZA (1) | ZA75780B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES517622A0 (en) * | 1982-11-23 | 1983-12-16 | Faes | PROCEDURE FOR PREPARING A NEW SPIRODEAN. |
| YU150489A (en) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | DEVICE FOR TESTING CLOTHES FOR WATERPROOFNESS |
| NZ292289A (en) * | 1994-08-24 | 1998-05-27 | Astra Ab | Spiro-azabicyclic compounds useful in treating cns disorder |
| DE102005030051A1 (en) * | 2005-06-27 | 2006-12-28 | Grünenthal GmbH | New substituted 1-oxo-3,8-diazospiro(4.5)-decan-2-one compounds are 5-hydroxy tryptamine uptake receptor inhibitors, useful to treat and/or prevent e.g. pain, migraine, chronic paroxysomal hemicrania, depression and asthma |
-
1974
- 1974-02-12 CH CH205374A patent/CH601304A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR257608A patent/AR207856A1/en active
- 1975-02-06 ZA ZA00750780A patent/ZA75780B/en unknown
- 1975-02-07 DE DE19752505143 patent/DE2505143A1/en not_active Withdrawn
- 1975-02-11 AU AU78069/75A patent/AU498871B2/en not_active Expired
- 1975-02-11 GB GB5852/75A patent/GB1495647A/en not_active Expired
- 1975-02-12 ES ES434650A patent/ES434650A2/en not_active Expired
- 1975-02-12 FR FR7504356A patent/FR2262666A2/fr active Pending
- 1975-02-12 BE BE153283A patent/BE825444R/en active
- 1975-02-12 JP JP50016977A patent/JPS50112376A/ja active Pending
- 1975-02-12 CA CA219,912A patent/CA1033363A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU498871B2 (en) | 1979-03-29 |
| ZA75780B (en) | 1976-01-28 |
| BE825444R (en) | 1975-05-29 |
| AR207856A1 (en) | 1976-11-08 |
| FR2262666A2 (en) | 1975-09-26 |
| CA1033363A (en) | 1978-06-20 |
| CH601304A5 (en) | 1978-07-14 |
| DE2505143A1 (en) | 1975-08-14 |
| GB1495647A (en) | 1977-12-21 |
| JPS50112376A (en) | 1975-09-03 |
| AU7806975A (en) | 1976-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD2A | Announcement of lapse in spain |
Effective date: 20170705 |