GB715424A - Improvements in n-acyl derivatives of iminodibenzyl and in their preparation - Google Patents

Improvements in n-acyl derivatives of iminodibenzyl and in their preparation

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Publication number
GB715424A
GB715424A GB17383/52A GB1738352A GB715424A GB 715424 A GB715424 A GB 715424A GB 17383/52 A GB17383/52 A GB 17383/52A GB 1738352 A GB1738352 A GB 1738352A GB 715424 A GB715424 A GB 715424A
Authority
GB
United Kingdom
Prior art keywords
iminodibenzyl
propionyl
butyryl
carbon atoms
dimethylamino
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
GB17383/52A
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 GB715424A publication Critical patent/GB715424A/en
Expired legal-status Critical Current

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Abstract

The invention comprises N-acyl derivatives of iminodibenzyl of the formula: <FORM:0715424/IV (b)/1> or salts thereof with organic or inorganic acids, wherein X represents a divalent saturated aliphatic radical containing not more than five carbon atoms and Am represents the radical of a secondary amine consisting of NH and two aliphatic hydrocarbon radicals, each containing not more than five carbon atoms, the radical of a tri-(lower alkyl)-ethylene-diamine, the lower alkyl radical containing not more than three carbon atoms, or the radical of an alkylene imine having five or six ring members. The compounds are prepared by reacting an N-(halogenalkanoyl)-iminodibenzyl, produced by acylating iminodibenzyl with reactive halogen fatty acid derivatives, with a secondary amine consisting of NH and two aliphatic hydrogen radicals, each containing not more than five carbon atoms, with a tri-(lower alkyl)-ethylene diamine, the lower alkyl radical containing not more than three carbon atoms, or with an alkylene imine having five or six ring members, in an inert solvent (e.g. benzene or homologues thereof) and in presence of an acid-binding agent such as an organic tertiary base (e.g. dimethyl aniline or pyridine), a suitable inorganic binding agent (e.g. sodium or potassium carbonate) or an excess of the amine used for the reaction. Lists of suitable starting materials are specified. The examples describe the preparation of N-(a -diethylamino-propionyl) - iminodibenzyl, N - (a - piperidino-propionyl) - iminodibenzyl, N - [a - (N1 - di-methylaminoethyl - N1 - methyl - amino)-propionyl] - iminodibenzyl, N - a - (pyrrolidino-propionyl) - iminodibenzyl, N - (a - dimethyl-amino - butyryl) - iminodibenzyl, N - [a - (di-ethylaminoethyl - N1 - ethyl - amino) - butyryl]-iminodibenzyl, N - (a - piperidino - butyryl)-iminodibenzyl, N - (dimethylamino - acetyl)-iminodibenzyl, N - (diethylamino - acetyl)-iminodibenzyl, N - (N1 - diethylaminoethyl-N1-ethylamino - acetyl) - iminodibenzyl, N - di-allyl - aminoacetyl - iminodibenzyl, N - dibutylaminoacetyl - iminodibenzyl, N - piperidinoacetyl - iminodibenzyl, N - (a - dimethylamino-propionyl) - iminodibenzyl, N - (b - dimethylamino - propionyl) - iminodibenzyl, N - (b -diethylamino - propionyl) - iminodibenzyl, N-(b - piperidino - propionyl) - iminodibenzyl, N - (b - diallylamino - propionyl) - iminodibenzyl, N - [b - (N1 - diethylaminoethyl - N1-ethylamino) - propionyl] - iminodibenzyl, N-(b - dimethylamino - butyryl) - iminodibenzyl, N - (b - pyrrolidino - butyryl) - iminodibenzyl, and N - [b - (N1 - dimethylaminoethyl - N1-methylamino) - butyryl] - iminodibenzyl. N - (halogen - alkanoyl) - iminodibenzyls are prepared by acylating iminodibenzyl with halogen fatty acid halides or the corresponding anhydrides in the presence or absence of, for example, pyridine or dimethyl aniline. The following are prepared or employed as starting materials in the examples: N-chloracetyl-, N-a - bromopropionyl -, N - a - bromobutyryl -, N - b - bromopropionyl -, and N - b - bromobutyryl-iminodibenzyl. Others are mentioned as suitable starting materials.
GB17383/52A 1951-07-11 1952-07-10 Improvements in n-acyl derivatives of iminodibenzyl and in their preparation Expired GB715424A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH715424X 1951-07-11

Publications (1)

Publication Number Publication Date
GB715424A true GB715424A (en) 1954-09-15

Family

ID=4531065

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17383/52A Expired GB715424A (en) 1951-07-11 1952-07-10 Improvements in n-acyl derivatives of iminodibenzyl and in their preparation

Country Status (1)

Country Link
GB (1) GB715424A (en)

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