13221-89-1

Basic information

• Product Name: Methyl 1-methyl-4-oxopiperidine-3-carboxylate
• Synonyms: methyl 1-methyl-4-oxopiperidine-3-carboxylate;3-METHOXYCARBONYL-1-METHYL-4-PIPERIDONE;1-methyl-4-oxo-3-piperidinecarboxylate;4-keto-1-methyl-nipecot methyl ester;methyl 1-methyl-4-oxo-3-piperidinecarboxylate(SALTDATA: HCl);Methyl 1-Methyl-4-oxo-3-piperidinecarboxylate
• CAS NO: 13221-89-1
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19
• Mol File: 13221-89-1.mol

Chemical Properties

• Melting Point: 186 °C
• Boiling Point: 255.337 °C at 760 mmHg
• Flash Point: 108.225 °C
• Appearance: /
• Density: 1.129 g/cm³
• PKA: 10.66±0.20(Predicted)
• CAS DataBase Reference: Methyl 1-methyl-4-oxopiperidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 1-methyl-4-oxopiperidine-3-carboxylate(13221-89-1)
• EPA Substance Registry System: Methyl 1-methyl-4-oxopiperidine-3-carboxylate(13221-89-1)

Safety Data

• Hazardous Substances Data: 13221-89-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 1-methyl-4-oxopiperidine-3-carboxylate is utilized as an intermediate in the synthesis of pharmaceuticals for its contribution to the creation of drugs with antiviral and anti-inflammatory properties. Its role in drug development is pivotal, enabling the production of medicinal compounds that address significant health concerns.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 1-methyl-4-oxopiperidine-3-carboxylate serves as a key intermediate in the synthesis of various agrochemicals, thereby playing a crucial role in the development of products that contribute to agricultural productivity and crop protection.
Used in Research Applications:
Methyl 1-methyl-4-oxopiperidine-3-carboxylate is also employed as a reagent and precursor in organic synthesis within research settings. Its application in research facilitates the exploration of new chemical pathways and the development of innovative synthetic methods, potentially leading to the discovery of new compounds with practical applications.

InChI:InChI=1/C8H13NO3/c1-9-4-3-7(10)6(5-9)8(11)12-2/h6H,3-5H2,1-2H3

Upstream product

• 105-71-5 3-methyl[(3-methoxy-3-oxopropyl)methylamino]propanoate 
• 1445-73-4 1-Methyl-4-piperidone 
• 616-38-6 carbonic acid dimethyl ester 
• 1555-58-4 Bis(2-cyanoethyl)methylamine 
• 3518-85-2 methylimine-N,N-dipropionate methyl ester 
• 124-41-4 sodium methylate 
• 74-89-5 methylamine 

Downstream Products

• 113091-10-4 1-benzyl-3-methoxycarbonyl-3-(2-methoxycarbonyl-ethyl)-1-methyl-4-oxo-piperidinium; chloride 
• 1445-73-4 1-Methyl-4-piperidone 
• 499-04-7 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid 
• 144564-24-9 (R)-3-Benzyl-1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 144564-24-9 (S)-3-Benzyl-1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester 
• 41838-46-4 4-Amino-1-methylpiperidine 
• 1515-27-1 1-methylpiperidin-4-one oxime 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 1522363-84-3 3a,3a'-methylenebis(5-methyl-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,5-c]pyridin-3-one) 
• 1522363-87-6 2-phenyl-3a,5-dimethyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridin-3-one 
• 1620234-42-5 (3Z)-1-methyl-3-(2-phenylhydrazinylidene)pyrrolidin-2-one 
• 1597450-13-9 methyl (4Z)-4-(2-phenylhydrazono)-3,4-dihydro-2H-pyrrole-5-carboxylate 
• 1522363-85-4 5-methyl-2-phenyl-3,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-3-one 
• 34737-83-2 1-methylpiperidin-4-one hydrochloride 

Relevant articles and documents

Synthetic method of arecoline

The invention discloses a synthetic method of arecoline. The synthetic method comprises the following steps: taking methyl 3-bromopropionate as an initial raw material, sequentially carrying out sodium methoxide claisen ester condensation, methylamine cyclization, sodium borohydride reduction and dehydration under alkaline conditions to obtain arecoline. According to the method, methyl 3-bromopropionate and a methylamine alcohol solution are used as the raw materials so that the problem that methyl iodide or highly toxic dimethyl sulfate with high cost is used in an N-methylation step, and the safety is controlled from the source is avoided.

Preparation method of mebhydrolin napadisylate

The invention belongs to the field of drug synthesis and provides a preparation method of mebhydrolin napadisylate. The preparation method is characterized by including the steps of firstly, subjecting methyl imine-N,N-methyl dipropionate and sodium methylate to heating under the effect of an organic solvent to achieve loop closing, and using hydrochloric acid to performing heating decarboxylationto obtain N-methyl-4-piperidone hydrochloride; subjecting phenylhydrazine and benzyl chloride to condensation under an alkaline condition to obtain benzyl phenylhydrazine; thirdly, mixing the N-methyl-4-piperidone hydrochloride solution and the benzyl phenylhydrazine, heating to generate mebhydrolin hydrochloride, adding disodium 1,5-naphthalenedisulfonate to obtain the mebhydrolin napadisylate.The preparation method is high in yield, mild in reaction conditions, convenient in intermediate purification and capable of satisfying the requirements of industrial production.

Essential structure of opioid κ receptor agonist nalfurafine for binding to κ receptor 1: Synthesis of decahydroisoquinoline derivatives and their pharmacologies

On the basis of the three-dimensional pharmacophore model of opioid κ agonists, we simplified the structure of nalfurafine (selective κ agonist) to find the essential structural moieties for binding the opioid receptors, especially κ receptor type. As a result, we found that the trans-fused decahydroisoquinoline derivatives without a phenol ring bound the opioid receptor in micromolar order and that both the amide side chain and the nitrogen substituted by the cyclopropylmethyl group were indispensable moieties for eliciting the κ selectivity. The simple decahydroisoquinoline without amide side chain also bound the opioid receptor without receptor type selectivity, suggesting that the message-address concept would be applicable to even these simple derivatives. These findings that the simple decahydroisoquinoline derivatives showed the affinities for the opioid receptors, especially some of the compounds showed κ selectivity, are the first example in the opioid field.

Synthesis and ligand binding studies of 4'-iodobenzyl esters of tropanes and piperidines at the dopamine transporter

Four analogs and two homologs of cocaine, designed as potent cocaine antagonists, were synthesized. The S(N)2 reaction between ecgonine methyl ester (13) or appropriately substituted piperidinol (19, 21) and appropriately substituted 4-indobenzoyl chloride gave 4-indobenzoyl esters of tropane and piperidines (5-8). 2'-Hydroxycocaine (9) was obtained from 2'- acetoxycocaine (12) by selective transesterification with MeOH saturated with dry HCl gas. 2'-Acetoxycocaine (12) was synthesized from acetylsalicyloyl chloride (23) and ecgonine methyl ester (13). The binding affinities of these compounds were determined at the dopamine transporter for the displacement of ([3H]WIN-35428. An iodo group substitution at the 4'-position of cocaine decreased dopamine transporter binding potency, while a hydroxy or acetoxy group at the 2'-position exhibited increased binding potency for the dopamine transporter compared to cocaine (10- and 3.58-fold, respectively). 2'- Hydroxylation also enhanced the binding potency of 4'-iodococaine (5) by 10- fold. Replacement of the tropane ring with piperidine led to poor binding affinities.