DE1948584C - Aromatic aminoketones and anticholinergic and hypotensive agents - Google Patents

Description

in which X is a halogen and R ₁ and R _{2 have} the same meaning as in formula 1, is treated.

The examples illustrate the invention.

example 1

1, S-Diphenyl ^ -dimethylaminoäthylpropanon- i
(Connection no. 1)

0.2 gAtom of potassium are dissolved in 250 ml of liquid ammonia, and it is for 5 minutes in Leave touch. Then 0.1 mol of 1,3-diphenyl-2-propenone-1 added in the course of about 10 minutes in the dry state or in solution in ether, and it is held in contact for 20 minutes. Then finally in the course of about 20 minutes 0.25 mol dimethylaminoethyl chloride added and left in contact for 3 hours. It is hydrolyzed with ammonium chloride and after evaporating the ammonia and adding water, extracted with ether. After concentric the ethereal phase is 1,3-Diphcnyl-3-dimethylaminoäthylpropanon-l isolated, which is purified by distillation under reduced pressure. The yield is 45%, bp = 163 to 165 ° C 0.2 mm Hg, F. = 52 "C.

The compounds given in the table below are prepared according to the above procedure manufactured.

connection
No. Ar ₁ = Ar ₂ -CH, R. N (C ₂ H ₅ ), yield
% Kp .. Omm Hg F., C 2 C ₆ H ₅ -CH ₂ -CH, - 57 195 to 197 / 0.2 3 -QH ₅ -CH ₂ -CH, - N O 47 205 to 203 / 0.2 54 4th C ₆ H ₅ - CH, - 51 210 to 211 / 0.2 66

Example 2

3-phenyl-1-p-methoxy phenyl-3-diethylamino-

ethyl propanone-1
(Compound no.5)

0.4 g of potassium are dissolved in 250 ml of liquid ammonia and left in contact for 5 minutes left. Then 0.1 mol of 3-phenyl-1-p-methoxyphynyl-2-propynon-1 added in the course of about 10 minutes in the dry state or in solution in ether, and it is in contact for 20 minutes held. Finally, 0.12 mol of diethylaminoethyl chloride are added in the course of about 20 minutes added and it is left in contact for 3 hours

left. It is hydrolyzed by anionic chloride and extracted after evaporation of the ammonia and addition of water with ether. After concentrating the ethereal phase is 3-phenyl-I-p-methoxyphenyl ^ -diäthylaminoäthylpropanon-1 isolated, which is purified by distillation under reduced pressure. The yield is 76%, Bp = 194 to 197 ° C / 0.1 mm Hg.

3-Phenyl-1-p-methoxyphenyl-3-pipendinoethylpropanon-1 (Compound No. 6) is obtained from 3-phenyl-1-p-methoxyphenyl-2-propenone-1 according to the same procedure and piperidinoethyl chloride produced. The yield is 74%, bp = 215 to 218 ° C / 0.1 mm Hg.

Example 3

Bis-l, 3- (p-methoxyphenyl) -3-diethylaminoethyl-

propanone-1
(Compound no.7)

0.6 g of potassium are dissolved in 250 ml of liquid ammonia and left in contact for 5 minutes left. Then 0,! Iviol Bis-1,3 (p-methoxyphenyl) -3-propenone-1,3 added in the course of about 10 minutes in the dry state or in solution in ether, and it is in contact for 20 minutes held. Finally, 0.12 mol of diethylaminoethyl chloride are added in the course of about 20 minutes, and it is left in contact for 3 hours. It is hydrolyzed by ammonium chloride and after evaporating the ammonia and adding water, extracted with ether. To Concentrating the ethereal phase is the bis;, 3 - (p - methoxyphenyl) - 3 - diethylaminoethylpropanon-1 isolated, which is purified by distillation under reduced pressure. The yield is 48%, bp = 215 to? .18 ° C / 0.1 mm Hg.

Bis-l, 3- (p-methoxyphenyl) -3-piperidinoethylpropanon-1 (Compound no. 8) is converted from bis-1,3- (p-methoxyphenyl) -2-propenone-1 according to the same procedure and Piperidinoäthylch'oiid produced. The yield is 42%, bp = 238 to 240 ° C / 0.1 mm Hg.

The compounds of general formula I according to the invention have a central and peripheral one anticholinergic activity as well as a hypotensive effect.

Claims (2)

Patent claims: 1. Aromatic aminoketones of the general formula Ar ₁ -C-CH ₂ -CO-Ar ₂
(CH ₂ ), The invention also relates to anticholinercic drugs and hypotensive agents containing an active ingredient of the general formula I. The amino ketones of the invention can be prepared by a process in which an aromatic Ketone of the general formula Ar ₁ -CH = CH-CO-Ar ₂ (II) in which Ar ₁ and Ar _{2 have} the meanings given for formula I,, '; duced and alkylated, then with an alkali metal (sodium or potassium) in liquid ammonia and then with a halide of the formula R, in which Ar ₁ and Ar ₂ , which can be identical or different, _{denote a phenyl or methoxyphenyl radical and R 1} and R ₂ denote a methyl or ethyl group, and R ₁ and R together with the nitrogen atom denote the piperidino or morpholino group. 2. Anticholinergic and hypotensive agents, characterized du ^r ch a content of an active ingredient of the Anr./ruchs 1 and a conventional carrier material. The invention relates to new aromatic aminoketones of the general formula Ar ₁ - CH - CH, - CO - Ar, (CH ₂ ), (I) R ₁ N
\ mean in the Ar ₁ and Ar _2, which may be the same or different, a phenyl or methoxyphenyl radical and R ₁ and R ₂ is a methyl or ethyl group, and R ₁ and R ₂ together with the Stickstoifatom a piperidino or morpholino. X - (CH ₂ ), - N (HD