US4220773A
Expired / Lapsed
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Process for the manufacture of aza-spirodecanes
Assignee: Hoechst AG
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Filing: 1979-08-06
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Granted: 1980-09-02
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Expires: 1999-08-06
Abstract
Abstract For preparing 1-oxa-diaza-oxo-spirodecanes of the formula ##STR1## where X≠Y, standing for ##STR2## either a polyalkylpiperidone-4-cyanohydrine is reacted with an aldehyde or a ketone, or a polyalkyl-piperidone-4 is reacted with an aldehyde or ketone-cyanohydrine in a liquid aliphatic carboxylic acid as solvent.
Inventors
- 👤 Hartmut Wiezer
- 👤 Helmut Korbanka
- 👤 Norbert Mayer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:25
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/22; C07D498/02; C07D498/10; C07D498/12; C07D498/20
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
361 words
A process for the manufacture of aza-spirodecanes of the formula (I) ##STR12## in which X and Y, being different, each are ##STR13## R 1 is hydrogen or C 1 -C 12 -alkyl R 2 and R 3 , either are identical and represent each hydrogen or a C 1 -C 5 -alkyl group R 4 being a methyl group in this case, or R 2 is hydrogen or C 1 -C 5 -alkyl, and R 3 and R 4 , together with the carbon atoms to which they are linked, form a C 5 - or C 6 -cycloalkyl group, or a group of the formula ##STR14## R 5 and R 6 being identical or different, each are hydrogen, C 1 -C 30 alkyl, a phenyl or naphthyl group being unsubstituted or substituted by chlorine or C 1 -C 4 -alkyl, or a phenylalkyl group being unsubstituted or substituted by C 1 -C 4 -alkyl; or R 5 and R 6 , together with the carbon atom linked to them are a C 5 -C 18 -cycloalkyl group being unsubstituted or substituted by up to four C 1 -C 4 -alkyl groups, or a group of the formula ##STR15## which comprises reacting a polyalkyl-piperidone-4-cyanohydrine of the formula (II) ##STR16## with an aldehyde or ketone of the formula (III) ##STR17## or reacting a polyalkyl-piperidone-4 of the formula (IV) ##STR18## with an aldehyde- or ketone-cyanohydrine of the formula (V) ##STR19## at a temperature of from 20° to 120° C. in the presence of an aliphatic carboxylic acid liquid at room temperature as solvent, and in the presence of an inorganic protonic acid; the carbonyl compounds (III) and (IV), respectively, being used in a 1- to 3-fold molar amount relative to the cyanohydrines (II) and (V), respectively, and the amount of protonic acid being chosen in such a manner that the piperidone-cyanohydrines (II) and the piperidones (IV), respectively, are present as salts, while the 0.5 to 2-fold molar amount relative to the cyanohydrine to be converted is present in addition, and by subsequently liberating the free base from the protonic acid salt of the intended azaspirodecane so obtained by treatment with a stronger base.
Claim 2
Dependent Claim
361 words
A process for the manufacture of aza-spirodecanes of the formula (I) ##STR12## in which X and Y, being different, each are ##STR13## R 1 is hydrogen or C 1 -C 12 -alkyl R 2 and R 3 , either are identical and represent each hydrogen or a C 1 -C 5 -alkyl group R 4 being a methyl group in this case, or R 2 is hydrogen or C 1 -C 5 -alkyl, and R 3 and R 4 , together with the carbon atoms to which they are linked, form a C 5 - or C 6 -cycloalkyl group, or a group of the formula ##STR14## R 5 and R 6 being identical or different, each are hydrogen, C 1 -C 30 alkyl, a phenyl or naphthyl group being unsubstituted or substituted by chlorine or C 1 -C 4 -alkyl, or a phenylalkyl group being unsubstituted or substituted by C 1 -C 4 -alkyl; or R 5 and R 6 , together with the carbon atom linked to them are a C 5 -C 18 -cycloalkyl group being unsubstituted or substituted by up to four C 1 -C 4 -alkyl groups, or a group of the formula ##STR15## which comprises reacting a polyalkyl-piperidone-4-cyanohydrine of the formula (II) ##STR16## with an aldehyde or ketone of the formula (III) ##STR17## or reacting a polyalkyl-piperidone-4 of the formula (IV) ##STR18## with an aldehyde- or ketone-cyanohydrine of the formula (V) ##STR19## at a temperature of from 20° to 120° C. in the presence of an aliphatic carboxylic acid liquid at room temperature as solvent, and in the presence of an inorganic protonic acid; the carbonyl compounds (III) and (IV), respectively, being used in a 1- to 3-fold molar amount relative to the cyanohydrines (II) and (V), respectively, and the amount of protonic acid being chosen in such a manner that the piperidone-cyanohydrines (II) and the piperidones (IV), respectively, are present as salts, while the 0.5 to 2-fold molar amount relative to the cyanohydrine to be converted is present in addition, and by subsequently liberating the free base from the protonic acid salt of the intended azaspirodecane so obtained by treatment with a stronger base.
Claim 3
Dependent Claim
18 words
The process as claimed in claim 1, wherein the aliphatic carboxylic acid serving as solvent is acetic acid.
Claim 4
Dependent Claim
19 words
The process as claimed in claim 1, wherein the inorganic protonic acid is sulfuric acid or gaseous hydrogen chloride.
References Cited (Backward Citations)
US4110334A
Cited
US4107139A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-02 | 1984-03-03 | 1984-09-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-02 | 1988-03-03 | 1988-09-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-02 | 1992-03-03 | 1992-09-02 | $7700.00 | Window Closed / Lapsed |