GB585994A - Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom - Google Patents

Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom

Info

Publication number
GB585994A
GB585994A GB15558/43A GB1555843A GB585994A GB 585994 A GB585994 A GB 585994A GB 15558/43 A GB15558/43 A GB 15558/43A GB 1555843 A GB1555843 A GB 1555843A GB 585994 A GB585994 A GB 585994A
Authority
GB
United Kingdom
Prior art keywords
phenyl
carbinol
benzyl
ether
alcohols
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
GB15558/43A
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
Priority to CH240142D priority Critical patent/CH240142A/en
Priority to CH240143D priority patent/CH240143A/en
Priority to CH233685D priority patent/CH233685A/en
Priority to CH240137D priority patent/CH240137A/en
Priority to CH240146D priority patent/CH240146A/en
Priority to CH240134D priority patent/CH240134A/en
Priority to CH240135D priority patent/CH240135A/en
Priority to CH240148D priority patent/CH240148A/en
Priority to CH240147D priority patent/CH240147A/en
Priority to CH240140D priority patent/CH240140A/en
Priority to CH240149D priority patent/CH240149A/en
Priority to CH240144D priority patent/CH240144A/en
Priority to CH240145D priority patent/CH240145A/en
Priority to CH240133D priority patent/CH240133A/en
Priority to CH240141D priority patent/CH240141A/en
Priority to CH240136D priority patent/CH240136A/en
Priority to CH240138D priority patent/CH240138A/en
Priority to CH240139D priority patent/CH240139A/en
Priority to CH269402D priority patent/CH269402A/en
Priority to CH269406D priority patent/CH269406A/en
Priority to CH267634D priority patent/CH267634A/en
Priority to CH269405D priority patent/CH269405A/en
Priority to CH269413D priority patent/CH269413A/en
Priority to CH269403D priority patent/CH269403A/en
Priority to CH269410D priority patent/CH269410A/en
Priority to CH269409D priority patent/CH269409A/en
Priority to CH269411D priority patent/CH269411A/en
Priority to CH269404D priority patent/CH269404A/en
Priority to CH269407D priority patent/CH269407A/en
Priority to CH269408D priority patent/CH269408A/en
Priority to CH269401D priority patent/CH269401A/en
Priority to CH269412D priority patent/CH269412A/en
Priority to US499708A priority patent/US2397799A/en
Priority to BE468051D priority patent/BE468051A/xx
Application filed by JR Geigy AG filed Critical JR Geigy AG
Priority to FR898245D priority patent/FR898245A/en
Priority to GB15558/43A priority patent/GB585994A/en
Publication of GB585994A publication Critical patent/GB585994A/en
Priority to NL136979A priority patent/NL64829C/xx
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/08—Heterocyclic 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
    • C07D295/084—Heterocyclic 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
    • C07D295/088—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aminoalkyl ethers of general formula <FORM:0585994/IV/1> wherein Ar represents an aromatic residue, Y represents a hydrocarbon radical and Z represents an N-disubstituted aminoalkyl residue, are obtained by etherifying an alcohol of general formula <FORM:0585994/IV/2> wherein Ar and Y are as above-defined, or a functional derivative thereof, with an N-disubstituted amino alcohol or its functional derivative. Quaternary ammonium derivatives thereof may be obtained. The process is effected by treating (a) reactive esters of a -substituted benzyl alcohols with amino alcohols disubstituted at the nitrogen atom, in presence of hydrogen halide-binding agents; (b) metal compounds, particularly the alkali salts, of a -substituted benzyl alcohols with reactive esters of the foregoing amino-alcohols, preferably while heating and stirring in an inert medium, e.g. benzene; (c) corresponding esterified a -substituted benzyl hydroxyalkyl ethers, e.g. halogenalkyl ethers, with secondary or tertiary amines (the latter leading to the quarternary ammonium compounds, which are also obtained by adding reactive esters such as alkyl, aralkyl and alkinyl halides, e.g. allyl bromide; aryl sulphonic esters and dialkyl sulphates. Halogenalkyl ethers of a -substituted benzyl alcohols are obtained by treating (a) reactive esters of such alcohols with alkylene halogen hydrins in presence of an acid-binding agent, or (b) a -substituted araliphatic alcohols with reactive esters of alkylene halogen hydrins. The term "a -substituted benzyl alcohols" implies the secondary alcohols obtained by introducing aliphatic, araliphatic, hydroaromatic or aromatic substituents into the CH2- group of benzyl alcohol, e.g. (a) by catalytically reducing the corresponding aralkylketones, or (b) by reacting the corresponding aldehydes and suitable halides in a Grignard synthesis. In examples: (1) pulverised sodamide in absolute benzene is heated at 60 DEG C. with n-propyl-phenyl-carbinol, prior to heating under reflux with b -chlorethyl diethylamine, treating with water and 10 per cent hydrochloric acid, basifying with potassium carbonate and distilling the ethereal extract in vacuo. The product is also obtained by treating sodium in a mixture of benzene and diethylamino ethanol with a -n-propyl-benzyl chloride, heating under reflux and processing to isolate the corresponding base; similar products are obtained, using methyl-, ethyl-, isopropyl-, isopentyl- and allyl phenyl-carbinol; (2) a -isobutyl-benzyl-(chlorethyl) ether is heated with excess diethylamine at 100-120 DEG C. in a sealed vessel to obtain a -isobutyl-benzyl-(diethylamino ethyl) - ether; (3) n - propyl - benzyl-(diethylamino ethyl)-ether and benzyl chloride are heated in chlorobenzene to obtain the corresponding quaternary salt, and a similar product is obtained, using ethyl iodide; (4) crude b -chloroethyl piperidine is heated with sodamide and n-propyl phenyl carbinol in absolute benzene, and the mixture is processed in the usual way to isolate the product; (5) g -chloropropyl diethylamine is heated with the sodium salt of isobutyl-phenyl-carbinol or sec.-butyl-phenyl-carbinol to isolate the corresponding bases; (6) b -chlorethyl diethylamine is heated at 90-100 DEG C. with sodium and benzohydrol to yield the corresponding ether, which is neutralized to obtain its hydrochloride; the corresponding cyclohexyl-phenyl-, and cycloheptyl-phenyl ethers are described; (7) isobutyl-o-methyl-phenyl-carbinol or sec.-butyl-o-methyl-phenyl-carbinol is added to sodamide in benzene, followed by b -chlorethyl diethylamine and heating under reflux to isolate the corresponding ethers. A table is appended, listing the physical properties of similar compounds according to the formula <FORM:0585994/IV/3> (8) n-propyl benzyl-carbinol, in benzene, is added to a suspension of sodamide in benzene, heating at 60 DEG C. and treating with b -chlorethyl diethylamine with subsequent refluxing to obtain the corresponding product. Analogously, phenyl-benzylcarbinyl-diethylaminoethyl ether is isolated. Further examples of products obtained by the processes of the invention are: styryl-benzyl- or chlorobenzyl-carbinyl-diethylaminoethyl ether, o- or p-tolyl benzyl carbinyldiethylamino or dimethylamino-ethyl ether and cyclohexyl- or cyclo - pentyl - benzylcarbinyl - diethyl- or dimethyl-amino ethyl ether. Iso-butyl-o-methyl-phenyl-carbinol is obtained from o-toluyl aldehyde and isobutyl bromide, applying a Grignard synthesis. The Specification as open to inspection under Sect. 91 comprises the manufacture of aminoalkyl ethers of the general formula <FORM:0585994/IV/4> (wherein X is the direct bond, or an organic residue which may contain hetero atoms; Y1 is hydrogen or as Y2, a hydrocarbon radical, and Ar and Z are as defined above), by etherifying an alcohol of the general formula <FORM:0585994/IV/5> (wherein Ar, X, Y1 and Y2 are as defined) in the manner set out above; it includes the following additional subject-matter: (1) producing a -isobutyl-benzyl-(chloro-ethyl)-ether, from (a) probutyl-phenyl-carbinol and ethylene dichloride, (b) glycol and a -isobutyl-benzyl chloride; (2) reacting sodamide, n-propyl-(phenylethenyl) - carbinol and b - chlorethyl - diethylamine and hydrogenating the product to obtain n-propyl-(phenylethyl)-carbin ether; (3) reacting sodamide, n - propyl - (phenoxy - methyl)-carbinol and b -chlorethyldiethylamine; (4) reacting sodamide, a -phenyl-b -cyclohexylethylalcohol and b - chlorethyldiethylamine. This subject-matter does not appear in the Specification as accepted.
GB15558/43A 1942-09-23 1943-09-22 Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom Expired GB585994A (en)

Priority Applications (37)

Application Number Priority Date Filing Date Title
CH240143D CH240143A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH233685D CH233685A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240137D CH240137A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240146D CH240146A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240134D CH240134A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240135D CH240135A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240148D CH240148A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240147D CH240147A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240140D CH240140A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240149D CH240149A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240144D CH240144A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240145D CH240145A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240133D CH240133A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240141D CH240141A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240136D CH240136A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240138D CH240138A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240139D CH240139A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH240142D CH240142A (en) 1942-09-23 1942-09-23 Process for the preparation of a basic aralkyl ether.
CH269408D CH269408A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269402D CH269402A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269405D CH269405A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269413D CH269413A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269403D CH269403A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269410D CH269410A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269409D CH269409A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269411D CH269411A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269404D CH269404A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269407D CH269407A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269406D CH269406A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269401D CH269401A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH269412D CH269412A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
CH267634D CH267634A (en) 1942-09-23 1943-08-11 Process for the representation of a basic ether.
US499708A US2397799A (en) 1942-09-23 1943-08-23 Amino-ethers and a process for their manufacture
BE468051D BE468051A (en) 1942-09-23 1943-09-20
FR898245D FR898245A (en) 1942-09-23 1943-09-22 Process for the preparation of amino-alkyl ether oxides derived from alcohols of the aromatic-aliphatic series
GB15558/43A GB585994A (en) 1943-09-22 1943-09-22 Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom
NL136979A NL64829C (en) 1942-09-23 1947-12-15

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB15558/43A GB585994A (en) 1943-09-22 1943-09-22 Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom

Publications (1)

Publication Number Publication Date
GB585994A true GB585994A (en) 1947-03-04

Family

ID=10061278

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15558/43A Expired GB585994A (en) 1942-09-23 1943-09-22 Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom

Country Status (1)

Country Link
GB (1) GB585994A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918567C (en) * 1949-01-19 1954-09-30 Koninklijke Pharma Fab Nv Process for the preparation of a p-alkylbenzhydryl-dialkylaminoalkyl ether or salts of this ether
US4827999A (en) * 1981-12-02 1989-05-09 Toyobo Petcord Co., Ltd. Polyester fiber having excellent thermal dimensional _ stability, chemical stability and high _ tenacity and process for the production thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE918567C (en) * 1949-01-19 1954-09-30 Koninklijke Pharma Fab Nv Process for the preparation of a p-alkylbenzhydryl-dialkylaminoalkyl ether or salts of this ether
US4827999A (en) * 1981-12-02 1989-05-09 Toyobo Petcord Co., Ltd. Polyester fiber having excellent thermal dimensional _ stability, chemical stability and high _ tenacity and process for the production thereof

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