US4596874A
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Synthesis of nitrone from secondary amine
Assignee: The University of Osaka
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Filing: 1984-03-08
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Granted: 1986-06-24
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Expires: 2004-03-08
Abstract
Abstract A nitrone is synthesized from a secondary amine by reacting a compound represented by the following general formula <IMAGE> wherein R1 and R2 mean individually a hydrogen atom or an alkyl or aryl group and R3 denotes an alkyl or aryl group with a peroxide in the presence of a catalyst selected from the group consisting of tungsten compounds, molybdenum compounds, vanadium compounds, titanium compounds, palladium compounds, rhodium compounds, ruthenium compounds and nickel compounds. This process provides the nitrone by one-step oxidation of the secondary amine.
Inventors
- 👤 Shun-Ichi Murahashi
- 👤 Hitoshi Mitsui
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:20
CPC Classifications
C; C07; C07D; C07D217/00; C07D217/02; C07D217/08; C07C; C07C291/00; C07C291/02
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
149 words
A process for synthesizing a nitrone from a secondary amine, which process comprises reacting a secondary amine represented by the formula: ##STR30## wherein R 1 and R 2 individually represent a hydrogen atom or saturated, unsaturated or cyclo-alkyl, phenyl, or benzyl group, R 3 denotes a saturated, unsaturated or cyclo-alkyl, phenyl or benzyl group, and two or three of said R 1 , R 2 and R 3 together may be optionally coupled optionally via one or more heteroatoms selected from the group of O, N and S to form a cyclic group of 5 to 7 members which may be additionally benzo-fused and which may optionally contain substituent groups with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a tungsten compound, molybdenum compound, vanadium compound and titanium compound, whereby a nitrone corresponding to said secondary amine is obtained in a single step.
Claim 2
Dependent Claim
149 words
A process for synthesizing a nitrone from a secondary amine, which process comprises reacting a secondary amine represented by the formula: ##STR30## wherein R 1 and R 2 individually represent a hydrogen atom or saturated, unsaturated or cyclo-alkyl, phenyl, or benzyl group, R 3 denotes a saturated, unsaturated or cyclo-alkyl, phenyl or benzyl group, and two or three of said R 1 , R 2 and R 3 together may be optionally coupled optionally via one or more heteroatoms selected from the group of O, N and S to form a cyclic group of 5 to 7 members which may be additionally benzo-fused and which may optionally contain substituent groups with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a tungsten compound, molybdenum compound, vanadium compound and titanium compound, whereby a nitrone corresponding to said secondary amine is obtained in a single step.
Claim 3
Dependent Claim
25 words
The process as claimed in claim 1, wherein the catalyst is vanadium pentoxide, acetylacetonatovanadium oxide, acetylacetonatomolybdenum oxide, titanium tetrabutoxide monomer, tungstic anhydride or sodium tungstate.
Claim 4
Dependent Claim
23 words
The process as claimed in claim 1, wherein the reaction is carried out at a temperature in the range of -10° C.-+150° C.
Claim 5
Dependent Claim
18 words
The process as claimed in claim 1, wherein the reaction is carried out in an N 2 atmosphere.
Claim 6
Dependent Claim
17 words
The process as claimed in claim 1, wherein the reaction is carried out in a polar solvent.
Claim 7
Dependent Claim
17 words
The process as claimed in claim 5, wherein the solvent is water, methanol, or a water-alcohol solvent.
Claim 8
Dependent Claim
30 words
The process as claimed in claim 1, wherein the secondary amine is selected from the group consisting of dibutylamine, diisopropylamine, dibenzylamine, benzylmethylamine, pyrrolidine, piperidine, 2-methylpiperidine, 1,2,3,4-tetrahydroisoquinoline, 1-(3-benzyloxy-4-methoxy)benzyl-7-benzyloxy-6-methoxy -1,2,3,4-tetrahydroisoquinoline; or 1-(3-hydroxy-4-methoxy)benzyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline.
Claim 9
Dependent Claim
27 words
The process as claimed in claim 1 in which said secondary amine is reacted with about 3 moles of said peroxide per mole of said secondary amine.
Claim 10
Dependent Claim
14 words
The process as claimed in claim 1 in which the catalyst is sodium tungstate.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-06-23 | 1989-12-23 | 1990-06-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-23 | 1993-12-23 | 1994-06-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-23 | 1997-12-23 | 1998-06-24 | $7700.00 | Window Closed / Lapsed |