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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-oxazines

Info

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
Application number
ES0247829A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CH Boehringer Sohn AG and Co KG
Original Assignee
CH Boehringer Sohn AG and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by CH Boehringer Sohn AG and Co KG filed Critical CH Boehringer Sohn AG and Co KG
Publication of ES247829A1 publication Critical patent/ES247829A1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/341,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/361,4-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.
ES0247829A 1958-03-13 1959-03-10 Improvements in or relating to the production of substituted tetrahydro-1,4-oxazines Expired ES247829A1 (en)

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
ES2687095T3 (en) * 2010-05-21 2018-10-23 Research Triangle Institute Phenylimorpholins and analogues thereof

Also Published As

Publication number Publication date
GB862198A (en) 1961-03-01

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