370-09-2

Usage

InChI:InChI=1/C10H14N2/c1-2-7-12(6-1)9-10-4-3-5-11-8-10/h3-5,8H,1-2,6-7,9H2

Upstream product

• 123-75-1 pyrrolidine 
• 500-22-1 3-pyridinecarboxaldehyde 
• 6959-48-4 3-chloromethylpyridinium chloride 
• 100-55-0 3-hydroxymethylpyridin 
• 609-36-9 rac-Pro-OH 
• 59-67-6 nicotinic acid 
• 3731-52-0 3-Aminomethylpyridine 
• 110-63-4 Butane-1,4-diol 
• 77727-88-9 (pyridin-3-yl)(pyrrolidin-1-yl)methanone 

Relevant academic research and scientific papers

Ruthenium and Iron-Catalysed Decarboxylative N-alkylation of Cyclic Α-Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives

A modular and waste-free strategy for constructing N-substituted cyclic amines via decarboxylative N-alkylation of α-amino acids employing ruthenium- and iron-based catalysts is presented. The reported method allows the synthesis of a wide range of five- and six-membered N-alkylated heterocycles in moderate-to-excellent yields starting from predominantly proline and a broad range of benzyl alcohols, and primary and secondary aliphatic alcohols. Examples using pipecolic acid for the construction of piperidine derivatives, as well as the one-pot synthesis of α-amino nitriles, are also shown.

Ruthenium-Catalyzed Regioselective 1,4-Hydroboration of Pyridines

Simple ruthenium precursor [Ru(p-cymene)Cl2]2 1 catalyzed regioselective 1,4-dearomatization of pyridine derivatives using pinacolborane is reported. Two catalytic intermediates, [Ru(p-cymene)Cl2Py] 2 and [Ru(p-cymene)Cls

Iridium-catalyzed decarboxylative N-alkylation of α-amino acids with primary alcohols

A new decarboxylative N-alkylation reaction of α-amino acids has been developed. A variety of tertiary amines were obtained in good to excellent yields via the decarboxylative N-alkylation reaction of α-amino acids with primary alcohols catalyzed by a CpIr complex. Georg Thieme Verlag Stuttgart New York.

7-Azabicyclo[2.2.1]heptane as a scaffold for the development of selective sigma-2 (σ2) receptor ligands

A series of N-substituted 7-azabicyclo[2.2.1]heptanes (12-17 and 22-25) and similarly substituted pyrrolidines (32-36 and 41-44) were synthesized as sterically-reduced, achiral analogs of adamantane- and trishomocubane-derived σ ligands. In vitro competition binding assays against σ receptors revealed that arylalkyl N-substituents conferred selectivity for the σ2 subtype, while alicyclic or polycarbocyclic substituents imparted high affinity for both subtypes. The σ2 binding and subtype selectivities of N-arylalkyl-7-azanorbornanes was generally greater than the analogously-substituted pyrrolidines, indicating that steric bulk and conformational restriction around the nitrogen atom are likely important for subtype discrimination.

An efficient synthesis of nitrogen heterocycles by Cp*Ir-catalyzed N-cycloalkylation of primary amines with diols

A new efficient method for the N-cycloalkylation of primary amines with diols catalyzed by a Cp*Ir complex have been developed. A variety of five-, six-, and seven-membered cyclic amines are synthesized in good to excellent yields in environmentally benign and atom economical manner with the formation of only water as a coproduct. A large scale synthesis of N-benzylpiperidine and a two-step asymmetric synthesis of (S)-2-phenylpiperidine using (R)-1-phenylethylamine as a starting primary amine have been also achieved.

Ruthenium Complex-Catalyzed N-Heterocyclization. Syntheses of N-Substituted Pyrroles and Pyrrolidines from 1,4-Diols and Primary Amines

2-Butyne-1,4-diol reacts with aliphatic amines in the presence of a catalytic amount of at 150 deg C to give N-alkylpyrroles in good yields. 1,4-Butanediol reacts with aromatic or aliphatic amines to give N-substituted pyrrolidines in excellent yields; and are the best catalysts for aromatic and aliphatic amines, respectively.The reaction of 2-butene-1,4-diol with alkyl amines gives a 1:1 mixture of N-substituted pyrroles and pyrrolidines in high yield.