90-84-6

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYLPROPION is used as an appetite depressant for the short-term management of obesity. It stimulates the secretion of norepinephrine, which helps in reducing appetite and promoting weight loss.
Used in Weight Loss Supplements:
DIETHYLPROPION is used as a weight loss supplement to help individuals control their appetite and lose weight more effectively.
Brand Names:
Some of the brand names for DIETHYLPROPION include Adiposan, Adipyn, Alipid, Amfepromone, Apisate, Bonumin, Brenalalit, Brendalit, Controlgras, D.i.p.n, Delgamer, Deramix, Dietec, Dietil Retard, Dietil-Retard, Lineal-Plus, Lineal-Rivo, Lineal-Valeas, Linea-Valeas, Lipomin, Liposlim, Menutil, Moderatan Diffucap, Nobensin-75, Nobensine, Nobesine-25, Nulobes, Perfamone, Prefamone, Redicres, Regenon Retard, Regibon, Sinapet, Slim-Plus, Super Emegrin, T-712, Tenuate Dospan, and Tenucap.

World Health Organization (WHO)

Amfepramone, a phenethylamine derivative introduced in 1957, is controlled under Schedule IV of the 1971 Convention on Psychotropic Substances. It remains available in many other countries with highly evolved drug regulatory authorities as an aid to weight reduction.(Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV), , , 1971)

InChI:InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

Upstream product

• 93-54-9 1-Phenyl-1-propanol 
• 109-89-7 diethylamine 
• 108-86-1 bromobenzene 
• 660-68-4 diethyl amine hydrochloride 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 873-66-5 1-propenylbenzene 
• 637-50-3 1-phenylpropene 
• 5265-18-9 (+/-)-cathinone 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 4061-29-4 N,N-diethylphenacylamine 

Downstream Products

• 4830-54-0 2-Diethylamino-1-phenyl-propan-1-ol 
• 4830-54-0 2-Diethylamino-1-phenyl-propan-1-ol 

Relevant academic research and scientific papers

Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers

The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

A five coordination Cu(II) cluster-based MOF and its application in the synthesis of pharmaceuticals: Via sp3 C-H/N-H oxidative coupling

Herein, a copper metal-organic framework, termed as VNU-18, containing penta-coordinated sites was successfully synthesized and fully characterized. This material was demonstrated to be an efficient heterogeneous catalyst for the oxidative C-H activation via N-H bonds. The optimized conditions are applicable for the synthesis of pharmaceuticals constructed by α-amino carbonyl skeletons.

1,3-Dibromo-5,5-dimethylhydantoin (DBH) mediated one-pot syntheses of α-bromo/amino ketones from alkenes in water

α-Bromo ketones are versatile intermediates of high practical utility. Traditional approaches to these compounds are restricted to a relatively hazardous/complex reagent combination, a long reaction time, the use of non-environmentally friendly solvents, or a limited substrate scope. Herein, we describe the development of a new methodology for the preparation of α-bromo ketones from alkenes using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a bromine source and an oxidant simultaneously. This easy to carry out two-step one-pot protocol proceeds in water and provides high yield of a great variety of α-bromo ketones. Addition of an amine to the intermediate α-bromo ketone further enables the preparation of α-amino ketones in a one-pot sequence.

Synthesis method of amfepramone hydrochloride drug intermediate 2-diethylamino-1-phenylacetone

The invention relates to a synthesis method of an amfepramone hydrochloride drug intermediate 2-diethylamino-1-phenylacetone, which comprises the following steps: adding 0.23 mol of alpha-aminophenylacetone into a reaction vessel which is provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, slowly adding 0.51-0.53 mol of diethylamine, heating the solution to 85-90 DEG C, reacting for 60-90 minutes, lowering the solution to 60-65 DEG C, adding 120ml of toluene, stirring for 60-80 minutes while controlling the stirring rate at 130-150 rpm, filtering, washing the filtrate with an oxalic acid solution, merging the extracting solutions, adding a potassium sulfite solution, regulating the pH value to 8-9, extracting with nitromethane 5-7 times, cooling the solution to 5-9 DEG C, precipitating a crystal, filtering, washing with a salt solution, washing with acetonitrile, and recrystallizing in cyclohexane to obtain the crystal 2-diethylamino-1-phenylacetone.

N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.

A two-step continuous synthesis of α-ketoamides and α-amino ketones from 2° benzylic alcohols using hydrogen peroxide as an economic and benign oxidant

A practical two-step synthesis of α-ketoamides and α-amino ketones via direct oxidative coupling between 2° benzylic alcohols and amines was developed. Hydrogen peroxide, an economic and environmentally friendly oxidant, was used, and a metal catalyst was unnecessary. Moreover, the continuous-flow technique was employed to increase the functional group tolerance, efficiency and safety.

Isolation and structural determination of non-racemic tertiary cathinone derivatives

The racemic tertiary cathinones N,N-dimethylcathinone (1), N,N-diethylcathinone (2) and 2-(1-pyrrolidinyl)-propiophenone (3) have been prepared in reasonable yield and characterized using NMR and mass spectroscopy. HPLC indicates that these compounds are isolated as the anticipated racemic mixture. These can then be co-crystallized with (+)-O,O′-di-p-toluoyl-d-tartaric, (+)-O,O′-dibenzoyl-d-tartaric and (-)-O,O′-dibenzoyl-l-tartaric acids giving the single enantiomers S and R respectively of 1, 2 and 3, in the presence of sodium hydroxide through a dynamic kinetic resolution. X-ray structural determination confirmed the enantioselectivity. The free amines could be obtained following basification and extraction. In methanol these are reasonably stable for the period of several hours, and their identity was confirmed by HPLC and CD spectroscopy.

A versatile and one-pot strategy to synthesize ?±-amino ketones from benzylic secondary alcohols using N -bromosuccinimide

A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important ?±-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, ?±-bromination of ketones, and nucleophilic substitution of ?±-bromo ketones to give ?±-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.

Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents

The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).