87462-06-4

Upstream product

• 1505-50-6 3-(4-Methylphenyl)propanoic acid 
• 74-89-5 methylamine 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 51-80-9 bis-(dimethylamino)methane 
• 124-40-3 dimethyl amine 
• 36627-00-6 N,N-dimethylaminomethyl iodide 

Relevant academic research and scientific papers

PRODUCTION OF AMINES VIA A HYDROAMINOALKYLATION REACTION

Provided is a process for producing an amine via a hydroaminoalkylation reaction of a non-aromatic C-C double bond or C-C triple bond, said process comprising a step of reacting a compound comprising a non-aromatic C-C double bond or C-C triple bond with a reactive component which is obtainable by combining an aminal or a hemiaminal ether with an acidic medium comprising trifluoroacetic acid, wherein the aminal contains two amino groups independently selected from a secondary and a tertiary amino group that are linked by a methylene group wherein one hydrogen atom may be replaced by a further substituent, and at least one of the amino groups carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the hemiaminal ether contains a secondary or a tertiary amino group which carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the secondary or tertiary amino group is linked to an alkoxy group by a methylene group wherein one hydrogen atom may be replaced by a further substituent.

A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes

In comparison to the extensively studied metal-catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench-stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.

Dimethylamine as a Substrate in Hydroaminoalkylation Reactions

Transition-metal-catalyzed hydroaminoalkylations of alkenes have made great progress over the last decade and are heading to become a viable alternative to the industrial synthesis of amines through hydroformylation of alkenes and subsequent reductive amination. In the past, one major obstacle of this progress has been an inability to apply these reactions to the most important amines, methylamine and dimethylamine. Herein, we report the first successful use of dimethylamine in catalytic hydroaminoalkylations of alkenes with good yields. We also report applicability for a variety of alkenes to show the tolerance of the reaction towards different functional groups. Additionally, we present a catalytic dihydroaminoalkylation reaction using dimethylamine, which has never been reported before.

A new series of estrogen receptor modulators that display selectivity for estrogen receptor β

A series of 1,3,5-triazine-based estrogen receptor (ER) modulators that are modestly selective for the ERβ subtype are reported. Compound 1, which displayed modest potency and selectivity for ERβ vs ERα, was identified via high-throughput screening utiliz

Competing Hydride Transfer and Ene Reactions in the Aminoalkylation of 1-Alkenes with N,N-Dimethylmethyleniminium Ions. A Literature Correction

A literature report that N,N-dimethylmethyleniminium ion (2) reacts with propylene and styrene to form unsaturated tertiary amines is shown to be incorrect.The major products are the secondary amines 1-(methylamino)butane and 1-(methylamino)-3-phenylpropane in which N-demethylation has occurred along with the saturation of the alkene.Analogous major products are formed with 1-butene, 1-hexene, 1-octene, 1-dodecene, 1-tetradecene, p-methylstyrene, and m-nitrostyrene as substrates.When the substrates are isobutylene, 2-ethyl-1-hexene, α-methylstyrene, and p-methoxystyrene, the major products are tertiary amines, but the secondary amines are also formed in smaller yields.The small yields of tertiary amines obtained in the cases of styrene and p-methylstyrene were increased by going from solvent acetic acid to acetonitrile and by increasing the branching of the alkyl groups on nitrogen.The internal olefins 5-decene and cyclohexene were far less reactive, giving only 3-4percent of amine products that were mainly tertiary in the former case and secondary in the latter.It is concluded that tertiary amine products are favored by an alkene structure and a solvent that favors the formation of a stable carbenium ion intermediate or a transition state with substantial carbenium ion character upon electrophilic attack of the iminium ion on the alkene.The secondary amine products are favored when a carbenium ion is of low stability and when the β-carbon atom of the olefin and/or the alkyl group attached to nitrogen is sterically unhindered; such hindrance decreases the rate of hydride ion transfer that is believed to occur in the production of secondary amines.