GB793852A - Manufacture of new 3-amino-indanes - Google Patents

Manufacture of new 3-amino-indanes

Info

Publication number
GB793852A
GB793852A GB26766/54A GB2676654A GB793852A GB 793852 A GB793852 A GB 793852A GB 26766/54 A GB26766/54 A GB 26766/54A GB 2676654 A GB2676654 A GB 2676654A GB 793852 A GB793852 A GB 793852A
Authority
GB
United Kingdom
Prior art keywords
indane
substituted
aminoindane
ammonia
dimethyl
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
GB26766/54A
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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 Schering AG filed Critical Schering AG
Priority to GB26766/54A priority Critical patent/GB793852A/en
Publication of GB793852A publication Critical patent/GB793852A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
    • C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention comprises 3-amino-indane derivatives of the formula <FORM:0793852/IV (b)/1> in which R indicates hydrogen or a low alkyl radical, i.e. containing 1 to 4 carbon atoms, R1 indicates a low alkyl radical and Am is an unsubstituted amino group or an amino group mono- or di-substituted by low alkyl radicals, or a group attached by nitrogen which is a member of a 5- or 6-membered saturated heterocyclic ring. Such compounds are obtained when (a) 3-halogen-indanes appropriately substituted in the 1-position are reacted, preferably in the absence of water, with ammonia or an appropriate primary or secondary amine; or (b) a 3-keto indane appropriately substituted in the 1-position is either (a ) first reacted with hydroxylamine to give its oxime and the latter then reduced to the amine; or (b ) directly subjected to reductive amination in the presence of ammonia or a corresponding primary or secondary amine, whereupon, if desired, the primary or secondary amine obtained according to one of the specified methods is converted by N-alkylation into the finally desired N-substituted 3amino-indane. The 1-substituted 3-halogenoindanes can be obtained by catalytic reduction of the corresponding indane-3-ones, and reaction of the indane-3-ols produced with halogenating agents such as thionyl chloride. As amines for the introduction of the group Am there are mentioned mono- and di-alkylamines, piperidine, pyrrolidine, morpholine, oxazolidine, thiazolidine and piperazine. In examples: (2 and 3) 1:1-dimethylindanone-(3) oxime (prepared from the ketone) is reduced to 1:1-dimethyl-3-aminoindane with palladium black and Raney nickel respectively. In further examples there are prepared by hydrogenation of a mixture of the appropriate indanone and the amine or ammonia (1) 1-methyl-3-methylamino - indane; (4) 1:1 - dimethyl - 3 - aminoindane. In Example (5) 1:1 dimethyl-3-aminoindane is dimethylated with formic acid and formaldehyde.
GB26766/54A 1954-09-15 1954-09-15 Manufacture of new 3-amino-indanes Expired GB793852A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB26766/54A GB793852A (en) 1954-09-15 1954-09-15 Manufacture of new 3-amino-indanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB26766/54A GB793852A (en) 1954-09-15 1954-09-15 Manufacture of new 3-amino-indanes

Publications (1)

Publication Number Publication Date
GB793852A true GB793852A (en) 1958-04-23

Family

ID=6710391

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26766/54A Expired GB793852A (en) 1954-09-15 1954-09-15 Manufacture of new 3-amino-indanes

Country Status (1)

Country Link
GB (1) GB793852A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101062897B (en) * 2006-04-25 2011-11-23 重庆医药工业研究院有限责任公司 Improved process for preparing 2,3-dihydro-1H-indenes-1-amine and derivative thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101062897B (en) * 2006-04-25 2011-11-23 重庆医药工业研究院有限责任公司 Improved process for preparing 2,3-dihydro-1H-indenes-1-amine and derivative thereof

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