10315-06-7

Basic information

• Product Name: METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE
• Synonyms: METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE;MethylN-benzylisonipecotinate;Methyl 1-benzyl-4-piperidinecarboxylate;Methyl-benzylpiperidine-4-carboxylate;N-Benzylisonipecotic acid methyl ester;1-benzyl-4-piperidinecarboxylate;Methyl N-benzylpiperidine-4-carboxylate;1-Benzyl-piperidine-4-carboxylic acid Methyl ester
• CAS NO: 10315-06-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.30616
• EINECS: 616-635-7
• Product Categories: Piperidine;Esters;Pyrans, Piperidines & Piperazines
• Mol File: 10315-06-7.mol

Chemical Properties

• Boiling Point: 310.755 °C at 760 mmHg
• Flash Point: 108.437 °C
• Appearance: White or off-white crystalline powder
• Density: 1.093 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: 2-8°C
• PKA: 7.86±0.10(Predicted)
• CAS DataBase Reference: METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE(10315-06-7)
• EPA Substance Registry System: METHYL 1-BENZYLPIPERIDINE-4-CARBOXYLATE(10315-06-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 10315-06-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C14H19NO2/c1-17-14(16)13-7-9-15(10-8-13)11-12-5-3-2-4-6-12/h2-6,13H,7-11H2,1H3

Upstream product

• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 2971-79-1 isonipecotic acid methyl ester 
• 498-94-2 isonipecotic acid 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 7462-86-4 methyl piperidine-4-carboxylate hydrochloride 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Downstream Products

• 67686-01-5 1-benzyl-4-piperidinemethanol 
• 681482-53-1 1-benzylpiperidine-4-carboxylic acid hydrochloride 
• 67686-03-7 1-benzyl-4-chloromethylpiperidine hydrochloride 
• 22065-85-6 N-benzyl-4-formylpiperidine 
• 255723-94-5 N-benzyl-4-[hydroxy(3-methoxyphenyl)methyl]piperidine 
• 255723-95-6 N-benzyl-4-(4-tert-butyl-3'-methoxybenzhydryl)piperidine 
• 352209-91-7 4-[4-(4-Chlorophenoxy)benzenesulfonyl]-1-benzylpiperidine-4-carboxylic acid methyl ester 
• 1057586-11-4 1-benzyl-4-[3-(5-bromo-2,3-dimethoxyphenyl)-[1,2,4]oxadiazol-5-yl]piperidine 
• 88915-26-8 4-aminomethyl-1-benzylpiperidine 
• 440101-15-5 tert-butyl (4-ethylpiperidin-4-yl)carbamate 
• 10315-07-8 N-benzylpiperidine-4-carboxylic acid 
• 183994-24-3 4-{bis[4-(trifluoromethyl)phenyl]hydroxymethyl}piperidine 
• 301219-50-1 1-(1-benzylpiperidin-4-yl)-3-phenylpropan-1-one 
• 62718-31-4 1-benzylpiperidine-4-carbonitrile 

Relevant articles and documents

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Synthesis method of N-benzyl-4-piperidine formaldehyde

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of N-benzyl-4-piperidine formaldehyde. According to the invention, 4-piperidinecarboxylic acid is used as a raw material; an esterification reaction is carried out to generate 4-methyl piperidinecarboxylate hydrochloride; an alkylation reaction is carried out on N-benzyl-4-methyl piperidinecarboxylate hydrochloride to generate N-benzyl-4-methyl piperidinecarboxylate; n-benzyl-4-methyl piperidinecarboxylate is hydrolyzed to obtain N-benzyl-4-piperidinecarboxylic acid, N-benzyl-4-piperidinecarboxylic acid is subjected to an acylation reaction to generate N-benzyl-4-piperidinecarboxamide, N-benzyl-4-piperidinecarboxamide is dehydrated to obtain 1-benzylpiperidine-4-nitrile, and 1-benzylpiperidine-4-nitrile is subjected to a reduction reaction to generate N-benzyl-4-piperidineformaldehyde. The method is mild in reaction condition, simple in aftertreatment and high in yield, N-benzyl-4-piperidinecarboxaldehyde can be obtained at the high yield at the temperature of 0 DEG C, column chromatography is not needed, and repeatability is high.

Production process of N-benzyl-4-methyl isonipecotate

The invention belongs to the technical field of pharmaceutical chemicals, and concretely relates to a production process of N-benzyl-4-methyl isonipecotate. The process comprises the following steps of reacting 4-methyl isonipecotate and benzyl chloride in a reaction solvent under an acid-binding agent condition, cooling after finishing raw material reaction, adding water for washing, drying and filtering an organic layer, and concentrating to obtain the N-benzyl-4-methyl isonipecotate. According to the process, 1,2-dichloroethane is adopted as a solvent for reaction, and the 1,2-dichloroethane obtained through concentration can be recycled, so that an environment-friendly performance is realized, and the raw material cost is greatly reduced.

Synthesis and evaluation of multi-target-directed ligands for the treatment of Alzheimer's disease based on the fusion of donepezil and melatonin

A novel series of compounds obtained by fusing the acetylcholinesterase (AChE) inhibitor donepezil and the antioxidant melatonin were designed as multi-target-directed ligands for the treatment of Alzheimer's disease (AD). In vitro assay indicated that most of the target compounds exhibited a significant ability to inhibit acetylcholinesterase (eeAChE and hAChE), butyrylcholinesterase (eqBuChE and hBuChE), and β-amyloid (Aβ) aggregation, and to act as potential antioxidants and biometal chelators. Especially, 4u displayed a good inhibition of AChE (IC50value of 193?nM for eeAChE and 273?nM for hAChE), strong inhibition of BuChE (IC50value of 73?nM for eqBuChE and 56?nM for hBuChE), moderate inhibition of Aβ aggregation (56.3% at 20?μM) and good antioxidant activity (3.28?trolox equivalent by ORAC assay). Molecular modeling studies in combination with kinetic analysis revealed that 4u was a mixed-type inhibitor, binding simultaneously to catalytic anionic site (CAS) and the peripheral anionic site (PAS) of AChE. In addition, 4u could chelate metal ions, reduce PC12 cells death induced by oxidative stress and penetrate the blood–brain barrier (BBB). Taken together, these results strongly indicated the hybridization approach is an efficient strategy to identify novel scaffolds with desired bioactivities, and further optimization of 4u may be helpful to develop more potent lead compound for AD treatment.

Preparation method of 1-benzyl-4-piperidine formaldehyde

The invention discloses a preparation method of 1-benzyl-4-piperidine formaldehyde. The preparation method comprises the following steps of carrying out a partial reduction reaction on 1-benzyl-4-piperidine methyl formate or 1-benzyl-4-piperidine ethyl formate and a vitride complex in a solvent; then collecting the 1-benzyl-4-piperidine formaldehyde from a reaction product. According to the preparation method of the 1-benzyl-4-piperidine formaldehyde, disclosed by the invention, 1-benzyl-4-piperidine formic acid esters are used as raw materials, the vitride complex is used as a reducing agent, the raw materials are easy to prepare, the operation is simple and convenient, the yield is high, the product purity is good, and the preparation method is suitable for industrial production.

Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols

Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.

Regioselective transformation of 6/5-fused bicyclic isoxazolidines to second-generation cyclic aldonitrones

The cycloaddition reactions of 4-(2-hydroxy-2-propyl)-3,4,5,6- tetrahydropyridine 1-oxide with mono- and di-substituted alkenes have been found to be highly stereo- as well as face-selective. In solution, the 6/5 fused bicyclic cycloadducts remain solely as the cis-fused invertomers in order to accommodate the bulky tertiary substituent 2-hydroxy-2-propyl in the equatorial orientation. The cycloadducts, upon peracid oxidation, leads to the exclusive formation of synthetically important second-generation cyclic aldonitrones. The stereo- and face-selectivity of the cycloaddition reactions of these second-generation nitrones bearing substituents at C(4) and C(6) have been briefly examined. One interesting finding was that treatment of the first generation nitrone i.e., 4-(2-hydroxy-2-propyl)-3,4,5,6-tetrahydropyridine 1-oxide, with mercury(II) oxide afforded a novel bicyclic nitrone, 1-oxa-5,6-dehydro-6-aza-bicyclo[3,2,1]heptane 6-oxide. ARKAT USA, Inc.

SUBSTITUTED 1-AMINOPHTHALAZINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC APPLICATION THEREOF

The invention concerns 1-amino-phthalazine derivatives of general formula (I): Wherein A, B, L, R, R1, R2, R3, R4, R5 and R7 are as defined herein. The invention also concerns the preparation of said compounds and their therapeutic use.

PYRAZOLOPYRIDINE DERIVATES

New compounds of formula (I) and the salts, solvates and prodrugs thereof, wherein the meanings for the various substituents are as disclosed in the description. These compounds are useful as p38 kinase inhibitors.