GB747768A - Reduction of aminoketones - Google Patents

Reduction of aminoketones

Info

Publication number
GB747768A
GB747768A GB18285/53A GB1828553A GB747768A GB 747768 A GB747768 A GB 747768A GB 18285/53 A GB18285/53 A GB 18285/53A GB 1828553 A GB1828553 A GB 1828553A GB 747768 A GB747768 A GB 747768A
Authority
GB
United Kingdom
Prior art keywords
noradrenaline
noradrenalone
bitartrate
oxalate
water
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
GB18285/53A
Inventor
Charles Aubrey Friedmann
Claude Wolfgang Picard
Fritz Fabian
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.)
CARNEGIES OF WELWYN Ltd
Original Assignee
CARNEGIES OF WELWYN 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
Application filed by CARNEGIES OF WELWYN Ltd filed Critical CARNEGIES OF WELWYN Ltd
Priority to GB18285/53A priority Critical patent/GB747768A/en
Publication of GB747768A publication Critical patent/GB747768A/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
    • 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
    • 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
    • C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

An organic acid salt of adrenalone or noradrenalone is catalytically hydrogenated to the salt of the corresponding amino alcohol in the form of a suspension or slurry in a medium in which the amino alcohol salt obtained is relatively more soluble. Specified organic acid salts are the oxalate and the tartrate, water being preferably used as the reaction medium for the oxalate and aqueous methanol, ethanol or isopropanol, containing preferably 10-40 per cent w./w. water, for the tartrate. The suspension or slurry may contain 15-30 per cent w./v. of the salt to be hydrogenated and the hydrogenation is preferably conducted at 40-60 DEG C. under slight superatmospheric pressure using a palladium-charcoal catalyst. The solutions of amino alcohol organic acid salts which are obtained may be decomposed with dilute ammonia to give the free bases. In examples: (1) adrenalone oxalate is suspended in water and reduced with hydrogen in the presence of a palladium-charcoal catalyst. Free d,l-adrenaline is recovered from the reaction mixture by standard procedure. (2) Noradrenalone oxalate is similarly reduced and d,l-noradrenaline is recovered. (3) Noradrenalone d-bitartrate is suspended in 80 per cent methanol and similarly reduced. The resulting solution is filtered and evaporated, and the residue on fractional crystallization from aqueous methanol gives d-noradrenaline-d-bitartrate as the less soluble fraction and l-noradrenaline d-bitartrate as the more soluble fraction. d-Noradrenaline and l-noradrenaline are recovered by treatment with aqueous ammonia and the l-noradrenaline is characterized by conversion to its hydrochloride. Noradrenalone-d-bitartrate is prepared from d-tartaric acid and noradrenalone hydrochloride. The Provisional Specification also refers to the use of other solvents, such as water, in the resolution of dl-noradrenaline-d-bitartrate, and to the use of platinum or Raney-nickel as hydrogenation catalysts in the reduction of dl-noradrenalone-d-bitartrate.
GB18285/53A 1953-07-01 1953-07-01 Reduction of aminoketones Expired GB747768A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB18285/53A GB747768A (en) 1953-07-01 1953-07-01 Reduction of aminoketones

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB18285/53A GB747768A (en) 1953-07-01 1953-07-01 Reduction of aminoketones

Publications (1)

Publication Number Publication Date
GB747768A true GB747768A (en) 1956-04-11

Family

ID=10109837

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18285/53A Expired GB747768A (en) 1953-07-01 1953-07-01 Reduction of aminoketones

Country Status (1)

Country Link
GB (1) GB747768A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013008247A1 (en) 2011-07-13 2013-01-17 Neon Laboratories Ltd. Process for preparation of (dl) -norepinephrine acid addition salt, a key intermediate of (r) - (-) - norepinephrine
CN108069863A (en) * 2016-11-17 2018-05-25 武汉武药制药有限公司 A kind of method for synthesizing norepinephrine
CN116082173A (en) * 2021-11-08 2023-05-09 武汉武药制药有限公司 Preparation method of dopamine hydrochloride

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013008247A1 (en) 2011-07-13 2013-01-17 Neon Laboratories Ltd. Process for preparation of (dl) -norepinephrine acid addition salt, a key intermediate of (r) - (-) - norepinephrine
CN108069863A (en) * 2016-11-17 2018-05-25 武汉武药制药有限公司 A kind of method for synthesizing norepinephrine
CN108069863B (en) * 2016-11-17 2020-08-11 武汉武药制药有限公司 Method for synthesizing norepinephrine
CN116082173A (en) * 2021-11-08 2023-05-09 武汉武药制药有限公司 Preparation method of dopamine hydrochloride

Similar Documents

Publication Publication Date Title
DE1963182C2 (en) 3- (3-Methylaminopropyl) -1-phenylindoline, process for its preparation and its use in combating depressive states
GB747768A (en) Reduction of aminoketones
DE69003570T2 (en) Hydrogenation of aromatic amines using rhodium supported on titanium dioxide or zirconium dioxide.
US2233128A (en) Process for the manufacture of benzidine
GB1371688A (en) Process for preparing benzoxazolones-2- and benzothiazolones-2
GB1494823A (en) Process for the production of 2-aryl-2h-benzotriazoles
Bostelaar et al. Effects of catalyst reduction and modification conditions on the enantioselectivity of Ni/SiO2 catalysts for liquid-phase hydrogenation of a prochiral keto compound
US2522858A (en) Hydrogenation of streptomycin
US3095448A (en) Cycloalkyl-alkyl hydrazines
GB1205285A (en) Process for preparing organic dinitriles from acrylonitrile
Schultz The Reaction of Aminoesters with Ethyl Isocyanate: Open Chain Models of Desthiobiotin
CH406175A (en) Process for the preparation of a reduction product of oxidized starch
SU117611A3 (en) The method of obtaining hydrospiramycin
US1951302A (en) Levo-compounds of the 1-hydroxyphenyl-2-aminopropan-1-ol series and process of preparing them
DE1568861C (en) Process for the production of cinnamon alcohol
DE2150975A1 (en) Nickel silica hydrogenation catalyst - of high specific surface,low alkali content for hydrogenating aldehydes,olefins
GB191326826A (en) Improvements in the Preparation of Ethyl Acetate from Acetaldehyde.
SU413978A1 (en)
GB801169A (en) Process for the preparation of 2 (alpha-aminoethyl)-furan and derivatives thereof
DE877756C (en) Process for the preparation of carbonic acid amides
CHEN et al. Catalytic Hydrogenation of Calcium D-Xylo-5-hexulosonate on Transition Metal Catalysts
DE963603C (en) Process for the preparation of 5, 6-dialkoxy-indoles
GB1106088A (en) Process for the preparation of phloroglucinol
GB530822A (en) Improvements in or relating to the production of a mixture of calcium d-gluconate and calcium l-idonate, and to the production of l-idonic acid and salts thereof
DE737640C (en) Process for splitting hydrocarbon oils or for pressure hydrogenation of coal, tars and mineral oils