GB778936A - Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls - Google Patents

Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls

Info

Publication number
GB778936A
GB778936A GB26972/55A GB2697255A GB778936A GB 778936 A GB778936 A GB 778936A GB 26972/55 A GB26972/55 A GB 26972/55A GB 2697255 A GB2697255 A GB 2697255A GB 778936 A GB778936 A GB 778936A
Authority
GB
United Kingdom
Prior art keywords
iminodibenzyl
dimethylaminopropyl
dichloro
hydrochloride
alkylene
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
GB26972/55A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB778936A publication Critical patent/GB778936A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0778936/IV(b)/1> wherein the alkylene radical has 2 to 6 carbon atoms and 2 to 4 bridging members, Am represents a dialkylamino radical with alkyl radicals having 1 to 3 carbon atoms or an alkylene imino radical with 5 or 6 ring members and X represents a halogen atom or a methyl group. Such compounds are obtained by reacting the appropriate substituted iminodibenzyl with a reactive ester of an alcohol of the general formula HO-alkylene-Am, and the products are if desired converted into their quaternary ammonium compounds or into their salts by treatment with halides or sulphates of aliphatic or araliphatic alcohols or with inorganic or organic acids. The dihalogeno- or dimethyl-iminodibenzyl is advantageously converted into its alkali salt by reaction with sodium, lithium or potassium amides or sodium or potassium metals. Iminodibenzyls having 3.7- or 1.9-dibromo, 2.8-, 3.7- or 1.9-dichloro or 3.7- or 2.8-dimethyl substituents are specified. They can be obtained by heating the corresponding substituted diamino-dibenzyls as diphosphates or in the presence of polyphosphoric acid. Salts mentioned are those with hydrochloric, hydrobromic, sulphuric, phosphoric, methane sulphonic, ethane disulphonic, acetic, citric, malic, succinic, tartaric, benzoic and phthalic acids. Examples describe the preparation of (1) 5-(b -dimethylaminopropyl) - 3.7 - dichloro - iminodibenzyl and its hydrochloride; (2) 5-(g -dimethylaminopropyl) - 3.7 - dichloroiminodibenzyl and its hydrochloride; 5-(b -piperidinoethyl)-3.7-dichloro-iminodibenzyl and its hydrochloride; 5 - (g - dimethylaminopropyl)-2.8 - dimethyliminodibenzyl; 5 - (b - pyrrolidinoethyl) - 3.7 - dibromo - iminodibenzyl. Specification 777,546 is referred to.
GB26972/55A 1954-09-22 1955-09-21 Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls Expired GB778936A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH778936X 1954-09-22

Publications (1)

Publication Number Publication Date
GB778936A true GB778936A (en) 1957-07-17

Family

ID=4536036

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26972/55A Expired GB778936A (en) 1954-09-22 1955-09-21 Improvements relating to n-aminoalkyl derivatives of substituted iminodibenzyls

Country Status (1)

Country Link
GB (1) GB778936A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108409660A (en) * 2018-05-14 2018-08-17 刘可 A kind of preparation method of antidepressant agents impurity isomers
CN108409659A (en) * 2018-05-14 2018-08-17 刘可 A kind of preparation method of antidepressant agents impurity isomers key intermediate
CN108707112A (en) * 2018-05-14 2018-10-26 刘可 A kind of preparation method of antidepressant agents impurity isomers chlorine nitre phenyl intermediates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108409660A (en) * 2018-05-14 2018-08-17 刘可 A kind of preparation method of antidepressant agents impurity isomers
CN108409659A (en) * 2018-05-14 2018-08-17 刘可 A kind of preparation method of antidepressant agents impurity isomers key intermediate
CN108707112A (en) * 2018-05-14 2018-10-26 刘可 A kind of preparation method of antidepressant agents impurity isomers chlorine nitre phenyl intermediates

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