GB765849A - Improvements in or relating to new aminoalkyl phenyl ethers - Google Patents

Improvements in or relating to new aminoalkyl phenyl ethers

Info

Publication number
GB765849A
GB765849A GB26040/53A GB2604053A GB765849A GB 765849 A GB765849 A GB 765849A GB 26040/53 A GB26040/53 A GB 26040/53A GB 2604053 A GB2604053 A GB 2604053A GB 765849 A GB765849 A GB 765849A
Authority
GB
United Kingdom
Prior art keywords
group
reacting
reaction
compounds
lower alkyl
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
GB26040/53A
Inventor
Peter Hey
George Lawrence Willey
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.)
University of Leeds
Original Assignee
University of Leeds
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 University of Leeds filed Critical University of Leeds
Priority to GB26040/53A priority Critical patent/GB765849A/en
Publication of GB765849A publication Critical patent/GB765849A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Landscapes

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

Abstract

The invention comprises compounds of the formula: <FORM:0765849/IV(b)/1> in which R1 and R2 are the same or different and are lower alkyl groups or chlorine atoms and R3 is a hydrogen atom or, where one or both of R1 and R3 are lower alkyl groups, a lower alkyl group, A represents a divalent group selected from -CH2-CH2-, <FORM:0765849/IV(b)/2> and R4 and R5 each represent a lower alkyl group (i.e. having up to 6 carbon atoms). Such compounds are obtainable by reacting a compound of the formula: <FORM:0765849/IV(b)/3> with a compound of the formula Y-Z where X, Y and Z represent atoms or groups such that X will react with Y-Z to form the group: <FORM:0765849/IV(b)/4> or a group readily convertible into such grouping, and in the latter case effecting such a conversion. "Convertible" groupings include -A-NH2, A.NHR4, -A-Halogen and A1CO. NR4R5 where A1 represents a group differing from A by a CH2 group. In the preferred process a phenol: <FORM:0765849/IV(b)/5> is reacted with a dialkylaminoalkyl halide of the formula Hal.A.NR3R4. Alternative methods are (a) reaction of the appropriate ester with an amine HNR4R5, (b) reduction of the corresponding amide, (c) alkylation of the corresponding primary or secondary amine. Where A is a branched chain, isomerization may occur during the reaction, the two isomers formed being separable by fractional crystalllization of their hydrochlorides. The starting materials can be prepared by reaction of the appropriate phenol ArOH with the appropriate basic ester to give Ar-O-A-NHR4 or Ar-O-A-NR4R5. Compounds of the type Ar-O-A-M (where M represents an ester group) are obtained by reacting the phenol with a diester M-A-M. Compounds of the type Ar-O-A1-CONR4R5 are obtained by reacting the appropriate phenol with an amide ester of the type M-A1-CONR4R5. In examples: (1) 2 - (b - dimethylaminoethoxy) - 1 : 3 - dichlorobenzene hydrochloride is prepared by the reaction of 2 : 6-dichlorophenol in aqueous sodium hydroxide solution with b -dimethylaminoethyl chloride hydrochloride; (2) the same product is obtained by reacting the sodium derivative of 2 : 6-dichlorophenol in acetone solution with an ethereal solution of b -dimethylaminoethyl chloride. Similarly obtained are (3) 2-(21-dimethylamino - 11 - methylethoxy) - 1 : 3 - dimethyl benzene hydrochloride (by fractional crystallization from the crude product from 2 : 6-xylenol and 3 - dimethylamino - 2 - chloropropane; (4) a mixture of 2 - (21 - diethylamino - 21-methylethoxy) - 1 : 3 - dimethylbenzene and 2-(21 - diethylamino - 11 - methylethoxy) - 1 : 3-dimethylbenzene (which is separated into its components by fractional crystallization) from 2 : 6-xylenol and 3-diethylamino-2-chloropropane hydrochloride; (5) b - (2 : 6 - xylyloxy)-ethyldimethylamine and b - (2 : 6 - xylyloxy) ethyldiethylamine, which are converted to hydrobromides. The two latter compounds can also be prepared by reacting the corresponding aryloxyethyl bromide with excess ethereal dimethylamine or diethylamine in a sealed ampoule at room temperature. The Provisional Specification also describes the reaction of 2 : 6-xylenol and 2 : 4 : 6-mesitol with 1 : 2-dibromoethane to give b -(2 : 6-xylyloxy)-ethyl bromide and b -(2 : 4 : 6-mesityloxy)-ethyl bromide respectively. Specification 687,189 is referred to.
GB26040/53A 1953-09-21 1953-09-21 Improvements in or relating to new aminoalkyl phenyl ethers Expired GB765849A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB26040/53A GB765849A (en) 1953-09-21 1953-09-21 Improvements in or relating to new aminoalkyl phenyl ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB26040/53A GB765849A (en) 1953-09-21 1953-09-21 Improvements in or relating to new aminoalkyl phenyl ethers

Publications (1)

Publication Number Publication Date
GB765849A true GB765849A (en) 1957-01-16

Family

ID=10237415

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26040/53A Expired GB765849A (en) 1953-09-21 1953-09-21 Improvements in or relating to new aminoalkyl phenyl ethers

Country Status (1)

Country Link
GB (1) GB765849A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1185196B (en) * 1959-05-29 1965-01-14 Sterling Drug Inc Process for the preparation of new aminoalkoxyaniline derivatives
US3205136A (en) * 1962-12-24 1965-09-07 Smith Kline French Lab Antidepressant phenyloxyalkylamines
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1185196B (en) * 1959-05-29 1965-01-14 Sterling Drug Inc Process for the preparation of new aminoalkoxyaniline derivatives
US3205136A (en) * 1962-12-24 1965-09-07 Smith Kline French Lab Antidepressant phenyloxyalkylamines
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US7223794B2 (en) 2001-07-31 2007-05-29 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
WO2003011210A3 (en) * 2001-07-31 2007-10-25 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase

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