[4-[2-(Diethylamino)ethoxy]phenyl]phenylmethanone

Orange Oil

(1) In a 250 ml three-necked flask equipped with a magnetic stirrer, a thermometer, a dropping funnel, and a condenser, 70 ml of acetone and 8.65 g (0.0437 mol) of 4-hydroxybenzophenone were added.Then pretreated 36.33g (0.1453mol exchange capacity)The D201FC exchange resin was added to a three-necked flask and stirred for heating.0.1 g of tetrabutylammonium bromide was added to the system.The system was heated to 30-40 °C.At this temperature, 5 g (0.0291 mol) of diethylaminochloroethane hydrochloride was added to the system and the addition was completed within ten minutes.Stirring was continued with stirring, and the reaction was monitored by HPLC, and the reaction was completed after 4 hours.Filtration was carried out, and the filtrate was distilled under reduced pressure to give about 15 g of a yellow oil. (2) To the oil was added 30 ml of methanol to dissolve, then 3.6 g of concentrated hydrochloric acid was added, and finally 45 ml of diethyl ether was added, which was formed as a white solid, and the upper liquid was pale yellow.Filter and wash the filter cake with ether. The finally obtained white solid was dissolved in 20 ml of water, and then adjusted to pH = 8 to 11 with a 2N sodium hydroxide solution of about 30 ml. (3) Extracted three times with methyl tert-butyl ether, 50 ml each time, and the organic phase was combined, washed once with saturated brine, and dried over 15 g of anhydrous sodium sulfate.After suction filtration and rotary evaporation, 8.32 g of 4-[2-(N, N-diethylamino)ethoxy]benzophenone was obtained.The yield was 96.27percent based on diethylaminochloroethane hydrochloride and the purity was 99.08percent.(1) In a 250 ml three-necked flask equipped with a magnetic stirrer, a thermometer, a dropping funnel, and a condenser, 70 ml of acetone and 8.65 g (0.0437 mol) of 4-hydroxybenzophenone were added.Then pretreated 36.33g (0.1453mol exchange capacity)The D201FC exchange resin was added to a three-necked flask and stirred for heating.0.1 g of tetrabutylammonium bromide was added to the system.The system was heated to 30-40 °C.At this temperature, 5 g (0.0291 mol) of diethylaminochloroethane hydrochloride was added to the system and the addition was completed within ten minutes.Stirring was continued with stirring, and the reaction was monitored by HPLC, and the reaction was completed after 4 hours.Filtration was carried out, and the filtrate was distilled under reduced pressure to give about 15 g of a yellow oil. (2) To the oil was added 30 ml of methanol to dissolve, then 3.6 g of concentrated hydrochloric acid was added, and finally 45 ml of diethyl ether was added, which was formed as a white solid, and the upper liquid was pale yellow.Filter and wash the filter cake with ether. The finally obtained white solid was dissolved in 20 ml of water, and then adjusted to pH = 8 to 11 with a 2N sodium hydroxide solution of about 30 ml. (3) Extracted three times with methyl tert-butyl ether, 50 ml each time, and the organic phase was combined, washed once with saturated brine, and dried over 15 g of anhydrous sodium sulfate.After suction filtration and rotary evaporation, 8.32 g of 4-[2-(N, N-diethylamino)ethoxy]benzophenone was obtained.The yield was 96.27percent based on diethylaminochloroethane hydrochloride and the purity was 99.08percent.4-(beta-Diethylaminoethoxy)-alpha-ethyl-benzhydrol Ethyl magnesium bromide is prepared from 3.88 g. of magnesium turnings and 17.44 g. of ethyl bromide in 60 ml. of anhydrous ether, the Grignard solution is cooled to -10° C., and a solution of 24 g. of 4-(beta-diethylaminoethoxy)-benzophenone in 120 ml. of dry ether is added dropwise. The reaction mixture is stirred vigorously, warmed to 0° C., stirred for 30 minutes at this temperature, and finally refluxed for 15 minutes. When the reaction is over -- which can be easily monitored by thin layer chromatography --, the mixture is poured onto ice water containing ammonium chloride. The etheral phase is separated, and the aqueous phase is extracted with 60 ml. of ether in two portions. The etheral solutions are combined, washed until neutral, dried over anhydrous magnesium sulfate, and evaporated to dryness. The solid residue is recrystallized from ethanol. This way 18.1 g. of 4-(beta-diethyl-aminoethoxy)-alpha-ethyl-benzhydrol are obtained, melting at 58°-59° C. Analysis: Calculated for C21 H29 NO2: C 77.02percent; H 8.93percent; N 4.28percent. Found: C 77.04percent; H 9.17percent; N 4.11percent. Characteristic IR absorption bands: 700, 755, 830, 1030, 1250, 3150 cm-1.4-(beta-Diethylaminoethoxy)-alpha-ethyl-benzhydrol Ethyl magnesium bromide is prepared from 3.88 g. of magnesium turnings and 17.44 g. of ethyl bromide in 60 ml. of anhydrous ether, the Grignard solution is cooled to -10° C, and a solution of 24 g. of 4-(beta-diethylaminoethoxy)-benzophenone in 120 ml. of dry ether is added dropwise. The reaction mixture is stirred vigorously, warmed to 0° C, stirred for 30 minutes at this temperature, and finally refluxed for 15 minutes. When this reaction is over -- which can be easily monitured by thin layer chromatography -- the mixture is poured onto ice water containing ammonium chloride. The etheral phase is separated, and the aqueous phase is extracted with 60 ml. of ether in two portions. The etheral solutions are combined, washed until neutral, dried over anhydrous magnesium sulfate, and evaporated to dryness. The solid residue is recrystallized from ethanol. This way 18.1 g. of 4-(beta-diethyl-aminoethoxy)-alpha-ethyl-benzhydrol are obtained, melting at 58°-59° C. Analysis: Calculated for C21 H29 NO2: C:77.02percent, H:8.93percent, N:4.28percent. Found: C:77.04percent, H:9.17percent, N:4.11percent. Characteristic IR absorption bands: 700, 755, 830, 1030, 1250, 3150 cm-1.

4-[2-(diethylamino)ethoxy]benzophenone is used in the preparation of antifertility agents.

Molecular Weight:297.4
XLogP3:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:8
Exact Mass:297.172878976
Monoisotopic Mass:297.172878976
Topological Polar Surface Area:29.5
Heavy Atom Count:22
Complexity:313
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes