7713-71-5

Usage

Uses

Used in Pharmaceutical Industry:
(1-METHYLAMINOPROPYL)BENZENE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs and medicinal compounds.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, (1-METHYLAMINOPROPYL)BENZENE serves as a key intermediate in the synthesis of a wide range of organic compounds. Its versatility in forming different chemical bonds and its compatibility with various reaction conditions contribute to its widespread use in this industry.
As a hazardous chemical, (1-METHYLAMINOPROPYL)BENZENE requires proper handling, storage, and disposal to minimize its potential risks to human health and the environment. Safety measures, such as wearing appropriate personal protective equipment and following established safety protocols, should be strictly adhered to when working with (1-METHYLAMINOPROPYL)BENZENE.

InChI:InChI=1/C10H15N/c1-3-10(11-2)9-7-5-4-6-8-9/h4-8,10-11H,3H2,1-2H3

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 622-29-7 N-Benzylidenemethylamine 
• 29640-04-8 N-(α-ethylbenzylidene)methylamine 
• 93-55-0 1-phenyl-propan-1-one 
• 74-89-5 methylamine 
• 74-85-1 ethene 
• 103-67-3 benzyl-methyl-amine 
• 10242-40-7 1,1-diethoxy-1-phenylpropane 
• 2941-20-0 1-phenylpropylamine 
• 591-51-5 phenyllithium 
• 593-51-1 methylamine hydrochloride 
• 83834-93-9 N-(1-phenylpropyl)formamide 
• 859314-73-1 ethyl-(1-phenyl-propenyl)-ether 

Downstream Products

• 133302-68-8 N-methyl-N-(trimethylsilylmethyl)-α-ethylbenzylamine 
• 29640-04-8 N-(α-ethylbenzylidene)methylamine 

Relevant academic research and scientific papers

Titanium-Catalyzed Hydroaminoalkylation of Ethylene

The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines

A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross-coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline. A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O was developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method was successfully applied to the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline.

Synthesis of N-methyl secondary amines

A diverse set of N-methyl secondary amines are obtained in high yields by an expedient reductive alkylation of commercially available methanolic methylamine.

Facile preparation of N-methyl secondary amines by titanium(IV) isopropoxide-mediated reductive animation of carbonyl compounds

A simple, mild and efficient procedure for obtaining N-methyl secondary amines from aldehydes and ketones is reported. Treatment of carbonyl compounds with methylamine hydrochloride, triethylamine and titanium(IV) isopropoxide, followed by in situ sodium borohydride reduction and straightforward aqueous work-up, affords clean products in good to excellent yields.

Asymmetric induction by chiral heterocyclic compounds: highly diastereoselective reaction of 5-oxa-7,8a-diazaperhydroazulen-8-ones with organometallic reagents

1) New chiral heterocyclic compounds, 5-oxa-7,8a-diazaperhydroazulen-8-ones (3a-c), were synthesized from (S)-prolinol (1) and potassium cyanate, followed by the condensation with aldehydes. 2) Extremely high diastereoselective reaction of the 3a-c with diethylzinc proceeded with a facil procedure to give (2S,1'S)-N-1'-arylpropyl-2-hydroxymethyl-1-pyrrolidinecarboxamide (4a-c). 3) The reduction of 4a-c with Red-Al gave (S)-1-aryl-N-methylpropylamines (5a-c) and (S)-prolinol (1) in good yields.

SYNTHESIS OF ARYLIMINES FROM N-SILYLAMIDES AND ARYLLITHIUM COMPOUNDS

Various arylimines were synthesized by the addition of N-silylated-N-alkyl- or N-aryl-amides to aryllithium compounds.