671-36-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 5279, 1957 DOI: 10.1021/ja01576a056

InChI:InChI=1/C7H15N/c1-7-5-3-4-6-8(7)2/h7H,3-6H2,1-2H3/t7-/m1/s1

Upstream product

• 109-06-8 α-picoline 
• 67-56-1 methanol 
• 77-78-1 dimethyl sulfate 
• 15032-01-6 1,6-dimethyl-1,2,3,4-tetrahydro-pyridine 
• 64-18-6 formic acid 
• 590-29-4 potassium formate 
• 71410-49-6 hex-5-ynyl-dimethyl-amine 
• 872-73-1 N-methyl-2-methylpyridinium iodide 
• 15938-10-0 1,2-dimethyl-pyridinium; bromide 
• 629-09-4 1,6-diiodohexane 
• 74-89-5 methylamine 
• 562-54-9 potassium methyl sulfate 
• 109-05-7 2-Methylpiperidin 
• 74-88-4 methyl iodide 

Downstream Products

• 101775-14-8 2-benzyl-1,2-dimethyl-piperidine 
• 91324-25-3 1-Methyl-3-acetylpiperidine 
• 2591-85-7 2-methylpiperidine-1-carbaldehyde 
• 109-05-7 2-Methylpiperidin 

Relevant academic research and scientific papers

Selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes and methylamines from cyclic amines and CO2/H2 catalyzed by an ionic liquid-Pd/C system

The reduction of CO2 with amines and H2 generally produces N-formylated or N-methylated compounds over different catalysts. Herein, we report the selective synthesis of formamides, 1,2-bis(N-heterocyclic)ethanes, and methylamines, which is achieved over an ionic liquid (IL, e.g., 1-butyl-3-methylimidazolium tetrafluoroborate, [BMIm][BF4])-Pd/C catalytic system. By simply varying the reaction temperature, formamides and methylamines can be selectively produced, respectively, in high yields. Interestingly, 1,2-bis(N-heterocyclic)ethanes can also be obtained via the McMurry reaction of the formed formamide coupled with subsequent hydrogenation. It was found that [BMIm][BF4] can react with formamide to form a [BMIm]+-formamide adduct; thus combined with Pd/C it can catalyze McMurry coupling of formamide in the presence of H2 to afford 1,2-bis(N-heterocyclic)ethane. Moreover, Pd/C-[BMIm][BF4] can further catalyze the hydrogenolysis of 1,2-bis(N-heterocyclic)ethane to access methylamine. [BMIm][BF4]-Pd/C was tolerant to a wide substrate scope, giving the corresponding formamides, 1,2-bis(N-heterocyclic)ethanes or methylamines in moderate to high yields. This work develops a new route to produce N-methylamine and opens the way to produce 1,2-bis(N-heterocyclic)ethane from cyclic amine as well.

Cold molten salt and storage device

One object is to provide a power storage device including an electrolyte using a room-temperature ionic liquid which includes a univalent anion and a cyclic quaternary ammonium cation having excellent reduction resistance. Another object is to provide a high-performance power storage device. A room-temperature ionic liquid which includes a cyclic quaternary ammonium cation represented by a general formula (G1) below is used for an electrolyte of a power storage device. In the general formula (G1), one or two of R1 to R5 are any of an alkyl group having 1 to 20 carbon atoms, a methoxy group, a methoxymethyl group, and a methoxyethyl group. The other three or four of R1 to R5 are hydrogen atoms. A? is a univalent imide anion, a univalent methide anion, a perfluoroalkyl sulfonic acid anion, tetrafluoroborate (BF4?), or hexafluorophosphate (PF6?).

Hydroamination/cyclization of aminoalkenes using cationic zirconocene and titanocene catalysts

Alternative catalysts: The hydroamination of nonactivated double bonds has been the domain of rare-earth-metal catalysts. Now alkyl zirconocene and titanocene cations, which are readily prepared from commercially available precursors, are shown to be active catalysts in the hydroamination/cyclization of secondary aminoalkenes to give tertiary pyrrolidines and piperidines.

Piperidylidene derivatives of cyano-5H-dibenzo[a,d]cycloheptene

Disclosed are 1-, 2-, or 3-cyano-N-alkyl-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds having pharmaceutical utility as tranquilizers; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when a tranquilizing effect is indicated.

Piperidylidene derivatives of carboxy-5H-dibenzo[a,d]cycloheptene

The new 1-alkyl-4-(1, 2, or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-one by reaction with a Grignard reagent prepared from a 1-alkyl-4-halo piperidine to form an intermediate carbinol, or a 1, 2 or 3-carboxy-5-(1-alkyl-4-piperidyl)-5H-dibenzo[a,d]cyclohepten-5-ol which is then dehydrated to produce the desired 1-alkyl-4-(1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, or alternatively by hydrolysis of a 1-alkyl-4-(1, 2 or 3-cyano-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compound to form the corresponding 1-alkyl-4-(1, 2 or 3-carboxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compound.

1 Alkyl-4-(10:oxo or hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds

The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobromination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.