Classifications

• • 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
  • C07C215/22—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 unsaturated
  • C07C215/28—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 unsaturated and containing six-membered aromatic rings
  • C07C215/30—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 unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton

Definitions

• the present invention relates to a process for the production of diamino-alcohols of the arcmatic series of the type:
• R4 hydrogen or a hydrocarbon radicle.
• the pro-v duction of said diamino-alcohols is efiected by treating aliphatic aromatic compounds, having one or two oxygen atoms in the side chain, with diamines in which 1 nitrogen atom is in tertiary, and the other in primary or secondary combination, the resulting reaction products being -re-" Jerusalem if necessary.
• the operations are performed in the manner customary for the production of the monoamino alcohols, such as ephedrin.
• the monoamines 1- phenyl-2(methyl-(diethylammoethyl))-aminopropane-l-ol 2.
• an aliphatic-aromatic a-dioxide compound, of the type R.CO.CO.X (in which R denotes an aromatic radicle and X hydrogen or methyl) be caused to react with diamines containing one nitrogen atom in tertiary, and the other in primary, combination, water is split off and a condensation product is obtained which furnishes the desired diamino-alcohol on reduction.
• the double linkage of the azornethine is saturated by hydrogen and, at the same time, the keto-group is converted into a secondary-alcohol group. 7
• Phenylpropandione brought into reaction in the aforesaid case are replaced by diamines, so that amino-alcohols with 2 nitrogen atoms result.
• the procedure according to the present invention consists in introducing the diamine, either in compounds already possessing alcohol character, or else'in compounds containing keto-groups which are afterwards reduced to alcoholgroups.
• the two working stages maybe combined, if the condensation of the keto-alcohol with the diamine be effected in presence of reducing agents.
• EXAlVl'PLE 2 (1 p-Methoxy-w- (methyl- (diethylaminoethyl) AMINOETHYL) )-AMINOETHANE-1-0L
• p-methoacy-w- (methyl- (diethylaminoethyl) aminoacetophenone 18.5 grams of p-methoxy-w-chloracetophenone (Ber. deutsch.chem.Ges., 30 (1897), p. 1715) are distributed in 50 cc. of benzene and gradually treated with 26 grams of a-methylamino-p-diethylaminoethane.
• the salt is very sparingly soluble in acetone. It is crystallized from a mixture of acetone with a small amount of alcohol, and melts, with decomposition, at 170-471 C. Yield: 25 grams of dihydrochloride (71% of the theoretical).
• the liquid is 11- tered and acidified, the methanol being distilled off and the solution repeatedly extracted with ether in order to remove non-basic constituents.
• the new base is taken up with ether and fractionated under a good vacuum. Under a pressure of about 0.5-1 mm. the racemic 1-phenyl-2- (diethylaminoethyl)aminopropane-1-ol passes over at about 140 C.
• the very sparingly soluble oxalate (melting point 180-182 C.) being precipitated.
• the free base is regenerated from the oxalate by means of alkali, then neutralized with hydriodic acid, brought to dryness and recrystallized from isopropyl alcohol. It melts at FIG-178 C.
• the residue is taken up with dilute hydrochloric acid, the aqueous acid solution is extracted with ether, to remove non-basic constituents, and after being rendered strongly alkaline with caustic potash, is again repeatedly extracted with ether.
• the liquid After the ether has been distilled oif, the liquid is heated at 100 C. for 1 hour with a threefold quantity of hydrobromic acid saturated at 0 C. When the liquid has cooled down, it is rendered alkaline, and the liberated base is fractionated in vacuo.
• the constituent passing over at 130- 135 C., under a pressure of about 1 mm., represents the desired racemic I-phenyl-Z-(methyl- (diethylaminoethyl) -aminopropane-1-ol.
• R denotes one element of the group consisting of phenyl and mono methoxy phenyl
• X one element of the group consisting of hydrogen and methyl
• R5 represents one element of the group consisting of hydrogen and methyl and subjecting the diamino-ketones thus obtained to a reduction.

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

Applications Claiming Priority (2)

Publications (1)

Family

ID=25926314

Family Applications (1)

Country Status (4)

Cited By (1)

• 1933
  • 1933-02-02 DE DEC47477D patent/DE629699C/de not_active Expired
• 1934
  • 1934-01-12 GB GB1171/34A patent/GB431786A/en not_active Expired
  • 1934-01-12 FR FR781017D patent/FR781017A/fr not_active Expired
  • 1934-01-12 GB GB10001/35A patent/GB431848A/en not_active Expired
  • 1934-01-26 US US708517A patent/US2046947A/en not_active Expired - Lifetime
• 1936
  • 1936-08-05 GB GB21574/36A patent/GB461866A/en not_active Expired

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