5379-88-4

Usage

InChI:InChI=1/C13H16N2O/c1-2-4-13-12(3-1)11(9-14-13)10-15-5-7-16-8-6-15/h1-4,9,14H,5-8,10H2

Upstream product

• 110-91-8 morpholine 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 7309-48-0 4-methoxymethyl-morpholine 
• 120-72-9 indole 
• 487-89-8 Indole-3-carboxaldehyde 
• 5472-71-9 1-(4-morpholinomethyl)-1H-benzotriazole 
• 75629-49-1 3-(morpholinomethylene)-3H-indole 
• 75-09-2 dichloromethane 
• 700-06-1 indole-3-carbinol 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

Bioactivity-guided synthesis of gramine derivatives as new MT1 and 5-HT1A receptors agonists

Twenty-four gramine derivatives were synthesized and evaluated on MT1 and 5-HT1A receptors in vitro. Among them, seven derivatives (7, 8, 16, 19, 20, 21, and 24) exhibited higher agonisting activities on MT1 or 5-HT1A

[Omim][Bf4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds

An efficient catalyst-free procedure has been developed for one-pot aminomethylation of some electron-rich aromatic compounds such as 1- and 2-naphthols, indole, N-methylindol and benzamide, in [omim][BF4] ionic liquid at room temperature. The ionic liquid can be recovered and reused without any noticeable loss of performance.

12-Tungstophosphoric acid immobilized on γ-Fe2O 3@SiO2 coreshell nanoparticles: An effective solid acid catalyst for the synthesis of indole derivatives in water

12-Tungstophosphoric acid immobilized on γ-Fe2O 3@SiO2 coreshell nanoparticles was used as novel solid acid catalyst for the synthesis of various bis(indolyl)methanes and β-functionalized indoles in water. The catalyst can

Hf(OTf)4-Catalyzed regioselective N -aminomethylation of indoles and related NH-containing heterocycles

Figure presented Under Lewis acidic conditions using Hf(OTf)4, the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.

Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology

The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.

Ruthenium-catalysed synthesis of tertiary amines from alcohols

Secondary amines have been converted into tertiary amines by reactions with primary alcohols. A catalytic system of [Ru(cymene)Cl2]2 with dppf has been shown to be effective for this transformation for a range of primary alcohols and secondary amines. The methodology has been applied to the one pot synthesis of Piribedil and other piperazine and morpholine-containing products.

Efficient and practical synthesis of Mannich bases related to gramine mediated by zinc chloride

An efficient and practical procedure for the Mannich reaction of secondary amine, formaldehyde, and indole or N-methylindole employing zinc chloride is presented. A series of gramine derivatives were obtained in 58-98% yields at room temperature in EtOH by using this method. Copyright Taylor & Francis Group, LLC.

A general synthesis of 1-(dialkylaminomethyl)indoles

1-(N,N-Dialkylamino)methylindoles are prepared from the corresponding 1-(dialkylaminomethyl)benzotriazoles by treatment with indole and base. The aminoalkylation proceeds in high yield with good regioselectivity.

Mannich Reactions Of Indoles With Dichloromethane And Secondary Amines Under High Pressure

Mannich reactions of indole with dichloromethane and secondary amines gave the corresponding Mannich bases in moderate to good yields, while 2-methylindole afforded only low yields of the Mannich bases.Some limitations were observed in the cases of hinder

PREPARATION AND REACTIONS OF 3-(AMINOMETHYLENE)-3H-INDOLES

A series of 3-(aminomethylene)-3H-indoles (1a-e and 6a-8a) was prepared by the condensation of 3-indolecarbaldehydes (2-5) with secondary amines.Among them, 3-(1-pyrrolidinylmethylene)-3H-indoles (1a and 6a-8a) were obtained as stable colorless prisms, while 3-(piperidinomethylene)-3H-indole (1b) and 3-(morpholinomethylene)-3H-indole (1c) readily polymerized in refluxing benzene.Reaction of 1 with electrophiles, such as alkyl and acyl halides, gave 1-substituted 3-aminomethylene-3H-indolium salts, which were converted to the corresponding 1-substituted 3-indolecarbaldehydes by hydrolysis.Reaction of 1 with active methylene compounds proceeded under mild reaction conditions to afford the corresponding condensation products in good yields.Successive reaction of 1 with electrophiles and nucleophiles provided a convenient route to 1,3-disubstituted indole derivatives.Keywords-conjugated enamine; 3-indolecarbaldehyde; 3-(aminomethylene)-3H-indole; 3-(aminomethylene)-3H-indolium salt; active methylene compounds; 3-(substituted vinyl)indole; gramine; electrophilic reaction; condensation