GB758382A - Improvements in bis-(ú­-aminophenoxy) alkane derivatives - Google Patents

Improvements in bis-(ú­-aminophenoxy) alkane derivatives

Info

Publication number
GB758382A
GB758382A GB56254A GB56254A GB758382A GB 758382 A GB758382 A GB 758382A GB 56254 A GB56254 A GB 56254A GB 56254 A GB56254 A GB 56254A GB 758382 A GB758382 A GB 758382A
Authority
GB
Grant status
Application
Patent type
Prior art keywords
bis
group
heptane
made
pentane
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
GB56254A
Inventor
Leslie Percy Walls
Clifford Gordon Raison
Thomas Marvel Sharp
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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

Links

Abstract

The invention comprises compounds of the formula (I) <FORM:0758382/IV(a)/1> and acid addition salts thereof, where R1 and R2 may be methyl, ethyl, propyl or allyl groups and n is 5, 7, 8 or 9 when R1 and R2 are both methyl, but is any integer from 5 to 9 in other cases. The compounds may be made from compounds of the formula (II) <FORM:0758382/IV(a)/2> where Z is a group convertible to -NR1R2, by effecting the required conversion, e.g. Z may be a quaternary ammonium hydroxide group which is converted by pyrolysis; a quaternary ammonium salt group which is converted by pyrolysis or by heating with alcoholic alkali or an alkali metal alcoholate; a quaternary ammonium salt group containing a benzyl group which is subjected to catalytic debenzylation, a primary or secondary amine group which is alkylated either directly or indirectly by heating with an alcohol in the presence of iodine, heating the hydrochloride salt in the presence of an alcohol or reductive alkylation in the presence of an aldehyde; a nitro group which is converted by reduction in the presence of an aldehyde; an alkylacylamino group which is reduced, suitably by means of lithium aluminium hydride, or a (carboxyalkyl) alkyamino group which is decarboxylated. The compounds of the formula (II) are made by reacting an a : o -disubstituted alkane of the formula (III) X-(CH2)n-X with a compound of the formula (IV) <FORM:0758382/IV(a)/3> where X and Y are groups capable of reacting together to form an ether linkage. In this reaction Z may be a tertiary amino group or a group convertible to a tertiary amino group; in the former case the desired product is obtained directly. Conveniently, Y may be a hydroxy group and X a halogen atom or an alkyl or aryl sulphonyloxy group. Preferred products include 1 : 7-bis-(p-dimethylaminophenoxy) heptane, 1 : 7-bis-(p-diethylaminophenoxy) heptane, 1 : 5 - bis - (p - methylethylaminophenoxy) pentane, 1 : 7 - bis - (p-methylethylaminophenoxy) heptane and 1 : 8-bis-(p-methylethylaminophenoxy) octane, and their acid addition salts. Many other products of the general formula (I) are exemplified. Starting materials. a : o -Bis-(p-diquaternaryammonium phenoxy) alkane salts such as 1 : 6-bis-(p-diethylaminophenoxy) hexane diethiodide, 1 : 6 - bis - (p - diethylaminophenoxy) hexane dimethiodide, 1 : 5-bis-(p-benzylmethyl-aminophenoxy) pentane dimethiodide, 1 : 8-bis - (p - diethylaminophenoxy) octane diethiodide, 1 : 7 - bis - (p - di - n - propylaminophenoxy heptane dimethiodide and 1 : 5-bis-(p - dimethylaminophenoxy) pentane dimethiodide are made by treating the appropriate bis-primary or secondary amine with an alkyl iodide. 1 : 5-Bis-(p-(carbethoxymethyl) methylaminophenoxy) pentane is made by the action of ethyl chloroacetate on 1 : 5-bis-(p-methylaminophenoxy) pentane in the presence of sodium acetate; hydrolsis of the ester gives the free acid. 1 : 7-Bis-(toluene-p-sulphonyloxy) heptane is made by treating 1 : 7-heptane diol with toluene-p-sulphonyl chloride in pyridine. 1 : 7 - Bis - (p - acet - methylamidophenoxy) heptane is made by the action of a mixture of acetic acid and acetic anhydride on 1 : 7 - bis - (p - methylaminophenoxy) heptane. 1 : 5 - Bis - (p - nitrophenoxy) pentane is made by the condensation of p-nitrophenol and 1 : 5-dibromopentane. Specification 636,648 is referred to.
GB56254A 1953-01-14 1953-01-14 Improvements in bis-(ú­-aminophenoxy) alkane derivatives Expired GB758382A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB56254A GB758382A (en) 1953-01-14 1953-01-14 Improvements in bis-(ú­-aminophenoxy) alkane derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB56254A GB758382A (en) 1953-01-14 1953-01-14 Improvements in bis-(ú­-aminophenoxy) alkane derivatives

Publications (1)

Publication Number Publication Date
GB758382A true true GB758382A (en) 1956-10-03

Family

ID=9706550

Family Applications (1)

Application Number Title Priority Date Filing Date
GB56254A Expired GB758382A (en) 1953-01-14 1953-01-14 Improvements in bis-(ú­-aminophenoxy) alkane derivatives

Country Status (1)

Country Link
GB (1) GB758382A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the preparation of new substituted aminophenols
EP0378457A2 (en) * 1989-01-12 1990-07-18 Sumitomo Chemical Company, Limited Aromatic allyl amine thermosetting resin composition
US5091582A (en) * 1987-04-25 1992-02-25 Bayer Aktiengesellschaft Process for the preparation of aromatic polyamines
US5221771A (en) * 1991-06-19 1993-06-22 Xoma Corporation Activated polymers and conjugates thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1144290B (en) * 1958-06-24 1963-02-28 May & Baker Ltd Process for the preparation of new substituted aminophenols
US5091582A (en) * 1987-04-25 1992-02-25 Bayer Aktiengesellschaft Process for the preparation of aromatic polyamines
EP0378457A2 (en) * 1989-01-12 1990-07-18 Sumitomo Chemical Company, Limited Aromatic allyl amine thermosetting resin composition
EP0378457A3 (en) * 1989-01-12 1991-10-09 Sumitomo Chemical Company, Limited Aromatic allyl amine thermosetting resin composition
US5109087A (en) * 1989-01-12 1992-04-28 Sumitomo Chemical Company, Limited Aromatic allyl amine thermosetting resin composition
US5221771A (en) * 1991-06-19 1993-06-22 Xoma Corporation Activated polymers and conjugates thereof

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