US3979379A
Expired / Lapsed
US
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Process for producing 1,3,5,7-tetraalkanoyl-1,3,5,7-octahydrotetrazocines
Assignee: United States Department of the Army
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Filing: 1975-04-25
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Granted: 1976-09-07
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Expires: 1995-04-25
Abstract
Abstract 1,3,5,7-Tetraalkanoyl-1,3,5,7-octahydrotetrazocines are produced in good yield by reacting a 1,5-dialkanoyl-1,3,5,7-tetraazabicyclo (3,3,1) nonane with an alkanoyl chloride, an alkanoic acid anhydride and an alkanoic acid alkali metal salt in the presence of an organic diluent.
Inventors
- 👤 Victor I. Siele
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 06:17
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
116 words
In the process for producing a 1,3,5,7-tetraalkanoyl-1,3,5,7-octahydrotetrazocine of the formula ##EQU1## wherein R is an alkyl group of 1 to 6 carbon atoms, which comprises reacting a 1,5-dialkanoyl-1,3,5,7-tetraazabicyclo (3,3,1) nonane of the formula ##EQU2## wherein R in both cases is the same and has the foregoing definition, with an alkanoyl chloride and an alkanoic acid anhydride of the formulas, resp. RCOCl and (RCO).sub.2 O wherein R in both cases is the same and has the foregoing definition, in the presence of an organic diluent, wherein the improvement comprises carrying out said reaction in the presence of an alkanoic acid salt of the formula RCOOMe, wherein R has the foregoing definition and Me is an alkali metal.
Claim 2
Dependent Claim
116 words
In the process for producing a 1,3,5,7-tetraalkanoyl-1,3,5,7-octahydrotetrazocine of the formula ##EQU1## wherein R is an alkyl group of 1 to 6 carbon atoms, which comprises reacting a 1,5-dialkanoyl-1,3,5,7-tetraazabicyclo (3,3,1) nonane of the formula ##EQU2## wherein R in both cases is the same and has the foregoing definition, with an alkanoyl chloride and an alkanoic acid anhydride of the formulas, resp. RCOCl and (RCO).sub.2 O wherein R in both cases is the same and has the foregoing definition, in the presence of an organic diluent, wherein the improvement comprises carrying out said reaction in the presence of an alkanoic acid salt of the formula RCOOMe, wherein R has the foregoing definition and Me is an alkali metal.
Claim 3
Dependent Claim
20 words
The process according to claim 1, wherein the reaction is carried out at a temperature between about 0° and 50°C.
Claim 4
Dependent Claim
13 words
The process according to claim 1, wherein the organic diluent is acetic acid.
Claim 5
Dependent Claim
12 words
The process according to claim 1, wherein the organic diluent is chloroform.
Claim 6
Dependent Claim
22 words
The process according to claim 1, wherein R is the same in each case except RCOOMe, in which R can be different.
Claim 7
Dependent Claim
34 words
The process according to claim 1, wherein the alkanoyl chloride, alkanoic acid anhydride and alkanoic acid salt are present in an amount of at least one mole per mole of the 1,5-dialkanoyl-1,3,5,7-tetraazabicyclo (3,3,1) nonane.
Claim 8
Dependent Claim
13 words
The process according to claim 1, wherein R in each case is methyl.
Claim 9
Dependent Claim
10 words
The process according to claim 7, wherein Me is sodium.
References Cited (Backward Citations)
CA590851A
Cited
US2941994A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-07 | 1980-03-08 | 1980-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-07 | 1984-03-08 | 1984-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-07 | 1988-03-08 | 1988-09-07 | $7700.00 | Window Closed / Lapsed |