ES247829A1 - Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines - Google Patents
Improvements in or relating to the production of substituted tetrahydro-1,4-oxazinesInfo
- Publication number
- ES247829A1 ES247829A1 ES0247829A ES247829A ES247829A1 ES 247829 A1 ES247829 A1 ES 247829A1 ES 0247829 A ES0247829 A ES 0247829A ES 247829 A ES247829 A ES 247829A ES 247829 A1 ES247829 A1 ES 247829A1
- Authority
- ES
- Spain
- Prior art keywords
- benzyl
- phenyl
- methyl
- formic acid
- acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises 2-phenyl-4-benzyl-, 2 - methyl - 3 - phenyl - 4 - benzyl -, 2 - (p - chlorophenyl) - 4 - benzyl -, 2 - phenyl - 3 - benzyl - 4 - methyl -, 2 - (5,6,7,8 - tetrahydronaphthyl - 2) - 3,4 - dimethyl -, and 2 - (m - hydroxyphenyl) - 3 - methyl -, 1,4 - oxazines, 2 - (p - methoxyphenyl) - 3 - methylmorpholine and their acid addition salts. In general tetrahydro-1,4-oxazines of the general formula <FORM:0862198/IV (b)/1> are produced by heating an a -(ethanolamino)-ketone of general formula <FORM:0862198/IV (b)/2> or a salt thereof with formic acid or a compound yielding formic acid under the reaction conditions, R1 being alkyl, aryl or aralkyl and R2, R3, R4 and R5 representing hydrogen or alkyl, aryl or aralkyl residues, and in which R1, R2, R3, R4 and R5 may be the same or different and may be substituted. The process is particularly useful for the production of those compounds in which R1 is a methyl, phenyl, chlorophenyl, methoxyphenyl, hydroxyphenyl or tetrahydronaphthyl radical and R2, R3, R4 and R5 are hydrogen atoms or methyl, phenyl or benzyl radicals. Substances yielding formic acid under the reaction conditions are, for example, formamide or dimethylformamide. The process may be carried out in a solvent medium, e.g. 70-100% aqueous formic acid an amide such as acetamide, dimethylformamide or dimethylacetamide a urea derivative such as N,N1-dimethylurea or an amine such as aniline, dimethylaniline, benzylamine or pyridine. The preferred temperature range for the process is 130-140 DEG C. It is advantageous to add an esterification catalyst such as, for example, perchloric acid, trichloracetic acid, p-toluene sulphonic acid, strongly acidic ion-exchangers, zinc chloride or boron trifluoride. If in the product R3 is a benzyl group or if any of the groups R2, R4 or R5 is a benzyloxy-phenyl residue these may be catalytically hydrogenated to replace the benzyl groups by hydrogen. Specification 791,416 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE862198X | 1958-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES247829A1 true ES247829A1 (en) | 1960-03-16 |
Family
ID=6797453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0247829A Expired ES247829A1 (en) | 1958-03-13 | 1959-03-10 | Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES247829A1 (en) |
| GB (1) | GB862198A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011255276B2 (en) * | 2010-05-21 | 2016-09-22 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| AU2011255456B2 (en) | 2010-05-21 | 2017-01-19 | Dignity Health Doing Business As St. Joseph's Hospital And Medical Center And Barrow Neurological Institute | 1 - phenylmorpholine derivatives as hydroxybupropion analogues for treating drug dependence |
-
1959
- 1959-03-10 ES ES0247829A patent/ES247829A1/en not_active Expired
- 1959-03-11 GB GB8413/59A patent/GB862198A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB862198A (en) | 1961-03-01 |
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