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

Definitions

• phenyl acetic acids and of their hydrogenation products have become known as compounds having neurotropic, atropine-like properties.
• R, R and R meaning the same or difierent saturated or unsaturated alkyl radicals.
• the tertiary trialkyl acetic acids which are used as starting material may be obtained by alkylating the nitrilesof monoor dialkyl acetonit'riles in the-presence of sodium amide according toZiegler, Annalen der Chemie, vol. 495, page 84- or German Patent 570,59i and subsequent hydrolysis of the so-obtained nitriles with an alcoholic solution of sodium or potassium hydroxide at temperatures ranging up to 180 C.
• Reactive esters of amino alcohols falling within thescope of the invention are especially esters withv hydrogen halide acids, with aryl sulfonic acids and the like.
• a further object of the invention consists in converting aliphatic tertiary carboxylic acids reactive derivatives of the. aliphatic: tertiary carboxylic acids, i. e. their halides, esters:v or
• halogen alkyl esters it is advantageous to react alkylene halogen hydrines withaliphatic tertiary carboxylic acids or with their halides, esters or anhydrides in the presence or absence of condensation agents or to react alkylene halogen hydrines or alkylene dihalides with salts of the said acids, the hydroxyl groups which may be present in the so-obtained compounds being subsequently replaced by halogen.
• The. basic esters claimed herein are colorless oils which, in form of their salts with inorganic or'organic acids, are soluble in water.
• Example 1 9 parts of methyl-di-n-propyl acetic acid chloride areadded, while stirring, to 6 parts of diethyl-amino ethanol and the mixture is heated, under stirring, for a short time to C.
• Theclear; yellowish-brown solution is treated, advantageously still Warm, with water and the aqueous. solution is extracted several times with.
• solvent is distilled oil. The. residue boils. at.
• the piperidino ethanol ester of methyl-di-npropyl acetic acid forms a hydrochloride of the melting point of 153-155 C.
• Example 2 16 parts of methyl ethyl-n-butyl acetic acid are heated for 24 hours to boiling, while stirring, with 14 parts of ,8-chloroethyl diethylamine and with 20 parts of potassium carbonate in 250 parts by volume of dry acetic acid ester. After cooling the potassium chloride is filtered by suction, the residue is washed with acetic acid ester and the combined acetic acid ester solutions are treated with dilute hydrochloric acid. The resulting acid solution is extracted with ether, then the base is freed by addition of a potassium carbonate solution and extracted with ether. After drying of the etheral solution the solvent is distilled off. The residue boils at 11 mm. pressure at 137-139 C. v
• esters are obtained with the correspond- Example 3 35 parts of diethyl-n-butyl acetic acid chloride are caused to react in the presence of pyridine with 1'7 parts of ethylene chlorohydrine. After complete reaction the mixture is extracted with ether and water, the ethereal solution is dried and the solvent distilled off. The residue is fractionated in vacuo and 20 parts of the so-obtained diethyl-n-butyl acetic acid-c-chloroethyl ester are interacted in the heat with 14 parts of piperidine. The mixture is extracted with ether and water. After having dried the ethereal solution the solvent is distilled off. The residue boils at 11 mm. pressure at 146149 C.
• esters When using the corresponding acid chlorides, there may be obtained for instance the following esters:
• Example 4- 10 parts of methyl-di-isobutyl acetic acid chloride are brought to interaction with 5 parts of dimethylamino propanol and worked up in the manner described in Example 1.
• the dimethylaminopropanol ester of the methyl-di-isobutyl acetic acid is obtained in form of a colorless oil having the boiling point at 13 mm. pressure of 146-149 C.
• a basic ester of an aliphatic tertiary carboxylic acid of the formula wherein A1 and A2 each represents a lower alkyl group and A1 and A2 together contain from 5 to 8 carbon atoms, X represents a divalent radical selected from the group consisting of -CH2.CH2--, CH2.CH2.CH2 and radicals, and Am stands for the radical of a secondary amine selected from the group consisting of lower dialkyl amines and piperidine.
• a basic ester of an aliphatic tertiary carb'oxylic acid of the formula A1 Az-('1OO-OXAni wherein A1 represents an alkyl radical containing at least 3 and at most 5 carbon atoms, A2 represents an alkyl radical containing at least 2 carbon atoms, and A1 and A2 together contain from 5 to 8 carbon atoms, X represents a divalent radical selected from the group consisting of -CH2.CH2, CH2.CH2.CH2 and CHz-CH:
• Am stands for the radical of a secondary amine selected from the group consisting of lower dialkyl amines and piperidine.
• the piperidinoethanol ester of methyl-di-npropyl acetic acid of the formula being a. colorless oil of the boiling point of 157 C. at 11 mm. pressure and forming a hydro- 5 chloride of the melting point of 153-l55 C., possessing valuable therapeutic properties.
• the dimethylaminopropanol ester of methyl-di-isobutyl acetic acid of the formula being a. colorless oil of the boiling point of 146- 149 C. at 13 mm. pressure, possessing valuable therapeutic properties.
• the diethylaminoethanolester of methyl-npropyl-n-butyl acetic acid of the formula being a colorless oil of the boiling point of 147- 148 C. at 12 mm. pressure, possessing valuable therapeutic roperties.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Hydrogenated Pyridines (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4464777

Family Applications (1)

Country Status (4)

Cited By (7)

Families Citing this family (1)

Citations (1)

• 1943
  • 1943-08-04 CH CH245220D patent/CH245220A/de unknown
• 1944
  • 1944-08-03 BE BE457094A patent/BE457094A/fr unknown
  • 1944-08-03 FR FR906284D patent/FR906284A/fr not_active Expired
  • 1944-08-14 US US549492A patent/US2460182A/en not_active Expired - Lifetime

Patent Citations (1)

Also Published As

Similar Documents