5773-58-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-4-piperidone is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of anesthetics, analgesics, and antipsychotic drugs. Its presence in these compounds aids in achieving the desired therapeutic effects and properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Methyl-4-piperidone serves as a crucial building block for the creation of compounds that are utilized in the development of pesticides and other agricultural chemicals, enhancing crop protection and yield.
Used in Chemical Synthesis:
3-Methyl-4-piperidone is used as a versatile intermediate in the synthesis of a wide range of organic compounds, demonstrating its adaptability across various chemical reactions and applications.
Used as a Solvent in Manufacturing:
3-Methyl-4-piperidone is utilized as a solvent in the production of resins, polymers, and coatings, where its properties contribute to the formation of high-quality end products with specific characteristics required by the industry.

InChI:InChI=1/C6H11NO/c1-5-4-7-3-2-6(5)8/h5,7H,2-4H2,1H3

Synthetic route

1-Benzyl-3-methyl-4-piperidon (34737-89-8) → 3-methyl-4-piperidone (5773-58-0)

Conditions	Yield
With palladium dihydroxide; hydrogen In ethanol under 2637.5 Torr; for 24h; Ambient temperature;	95%
With hydrogen; palladium on activated charcoal In ethanol under 2585.81 Torr;
With hydrogen; palladium dihydroxide In ethanol at 20℃; under 2585.81 Torr; for 4h;
With hydrogen; palladium on activated charcoal In methanol at 25℃; for 48h;

tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate (181269-69-2) → 3-methyl-4-piperidone (5773-58-0)

Conditions	Yield
Stage #1: tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: With water In dichloromethane; water	75%

5-diethylamino-2-methyl-pent-1-en-3-one (91016-40-9) → 3-methyl-4-piperidone (5773-58-0)

Conditions	Yield
With ammonia mit fluessigem Ammoniak;

3-methyl-4-piperidone (5773-58-0) + N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (1189852-14-9) + trifluoroacetic acid (76-05-1) → 4-(2-hydroxypropan-2-yl)-N-(7-(3-methyl-4-oxopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl)benzamide trifluoroacetate

Conditions	Yield
Stage #1: 3-methyl-4-piperidone; N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide In 1-methyl-pyrrolidin-2-one at 85℃; Stage #2: trifluoroacetic acid In 1-methyl-pyrrolidin-2-one; methanol; water; dimethyl sulfoxide; acetonitrile HPLC;	56%

3-methyl-4-piperidone (5773-58-0) + 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl bromide (84501-67-7) → 1-<2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl>-3-methyl-4-piperidone (173065-98-0)

Conditions	Yield
With sodium carbonate; sodium iodide In acetonitrile for 96h; Heating;	51%

3-methyl-4-piperidone (5773-58-0) + 1,2-Epoxy-3-menthyloxy-propan (2399-56-6) → C19H35NO3 (1253796-69-8)

Conditions	Yield
With water at 20℃; for 18h;	6%

3-methyl-4-piperidone (5773-58-0) + phenoxyamine hydrochloride (6092-80-4) → 4-methyl-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine (43213-62-3)

Conditions	Yield
With hydrogenchloride In ethanol Heating;

3-methyl-4-piperidone (5773-58-0) + 2-Chloromethyl-4,4-dimethyl-4H-1,3-benzothiazine (81735-43-5) → 2-(4'-Oxo-3'-methylpiperidino)methyl-4,4-dimethyl-4H-1,3-benzothiazine

Conditions	Yield
With sodium hydride In various solvent(s)

3-methyl-4-piperidone (5773-58-0) → 1-<2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl>-3-methyl-4-(4-bromo-2-fluoroanilino)piperidine

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent / NaI, Na2CO3 / acetonitrile / 96 h / Heating 2: 48 percent / NaBH3CN, 3 Angstroem molecular sieves, HCl(gas) / methanol / 96 h / Ambient temperature View Scheme

3-methyl-4-piperidone (5773-58-0) → bromobrifentanil

Conditions	Yield
Multi-step reaction with 3 steps 1: 51 percent / NaI, Na2CO3 / acetonitrile / 96 h / Heating 2: 48 percent / NaBH3CN, 3 Angstroem molecular sieves, HCl(gas) / methanol / 96 h / Ambient temperature 3: 38.8 percent / CH2Cl2 / 16 h / Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → brifentanil

Conditions	Yield
Multi-step reaction with 4 steps 1: 51 percent / NaI, Na2CO3 / acetonitrile / 96 h / Heating 2: 48 percent / NaBH3CN, 3 Angstroem molecular sieves, HCl(gas) / methanol / 96 h / Ambient temperature 3: 38.8 percent / CH2Cl2 / 16 h / Heating 4: tritium gas, Et3N / 5percent Pd/C / ethanol / 3 h / 24 °C View Scheme

3-methyl-4-piperidone (5773-58-0) → dimethyl-[2-(4-methyl-3,4-dihydro-1H-benzo[4,5]furo[3,2-c]pyridin-2-yl)-ethyl]-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: Na2CO3 / xylene / Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → dimethyl-[3-(4-methyl-3,4-dihydro-1H-benzo[4,5]furo[3,2-c]pyridin-2-yl)-propyl]-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: Na2CO3 / xylene / Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → 4-methyl-2-[3-(4-methyl-piperazin-1-yl)-propyl]-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: Na2CO3 / xylene / Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → 1-(4-fluoro-phenyl)-4-(4-methyl-3,4-dihydro-1H-benzo[4,5]furo[3,2-c]pyridin-2-yl)-butan-1-one

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: Na2CO3 / xylene / Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → 2-(3-chloro-propionyl)-4-methyl-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine (54995-92-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: aq. NaOH / benzene / 20 °C View Scheme

3-methyl-4-piperidone (5773-58-0) → 4-chloro-1-(4-methyl-3,4-dihydro-1H-benzo[4,5]furo[3,2-c]pyridin-2-yl)-butan-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / ethanol / Heating 2: aq. NaOH / benzene / 20 °C View Scheme

3-methyl-4-piperidone (5773-58-0) → 4-methyl-2-(3-pyrrolidin-1-yl-propionyl)-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / ethanol / Heating 2: aq. NaOH / benzene / 20 °C 3: Heating View Scheme

3-methyl-4-piperidone (5773-58-0) → 4-methyl-2-(4-pyrrolidin-1-yl-butyryl)-1,2,3,4-tetrahydro-benzo[4,5]furo[3,2-c]pyridine

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / ethanol / Heating 2: aq. NaOH / benzene / 20 °C 3: Heating View Scheme

3-methyl-4-piperidone (5773-58-0) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate (181269-69-2)

Conditions	Yield
With N,N-dimethylethylenediamine In dichloromethane at 20℃; for 2.5h;
With dmap; triethylamine In tetrahydrofuran; water at 20℃; for 18h;

3-methyl-4-piperidone (5773-58-0) + 2,3-dichloro-pyridine (2402-77-9) → 1-(3-chloropyridin-2-yl)-3-methylpiperidin-4-one (828266-05-3)

Conditions	Yield
In dimethyl sulfoxide at 85℃; for 12h;

3-methyl-4-piperidone (5773-58-0) + 4-chlorobenzyl bromide (622-95-7) → C13H16ClNO (1250946-51-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;

Upstream product

• 91016-40-9 5-diethylamino-2-methyl-pent-1-en-3-one 
• 34737-89-8 1-Benzyl-3-methyl-4-piperidon 
• 181269-69-2 tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate 

Downstream Products

• 181269-69-2 tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate 
• 1250946-51-0 C₁₃H₁₆ClNO 
• 1253796-69-8 C₁₉H₃₅NO₃ 

Relevant academic research and scientific papers

ANALGESIC THAT BINDS FILAMIN A

A compound, composition and method are disclosed that can provide analgesia. A contemplated compound has a structure that corresponds to Formula A, wherein A, B, X, R1, R2, R7 and R8, and the dashed lines are defined within.

AMINOPIPERIDINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC USE THEREOF

The present invention relates to compounds of formula (I) as defined herein that are melanocortin receptor agonists, to the preparation thereof and to the therapeutic use thereof in the treatment and in the prevention of obesity, diabetes and sexual dysfunctions that can affect both sexes, in the treatment of cardiovascular diseases, and also in anti-inflammatory uses or in the treatment of alcohol dependency.

THERAPEUTIC AGENTS USEFUL FOR TREATING PAIN

A compound of formula: wherein Ar1, Ar2, V, X, R3, R4, and m are as disclosed herein or a pharmaceutically acceptable salt thereof (a "Cyclo(hetero)alkenyl Compound"); compositions comprising an effective amount of a Cyclo(hetero)alkenyl Compound; and methods for treating or preventing, e.g., pain, UI, an ulcer, IBD, or IBS in an animal, comprising administering to an animal in need thereof an effective amount of a Cyclo(hetero)alkenyl Compound are disclosed herein.

HETEROARYLPIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of the formula (I): (wherein R>12345610 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

The synthesis of [fluorophenyl-3H(N)] ocfentanil and [fluorophenyl-3H(N)] brifentanil

[Fluorophenyl- 3H(N)] ocfentanil (1b) and [fluorophenyl - 3H(N)] brifentanil (2b) were synthesized by catalytic tritiation of appropriate bromo precursors (1a,2a). The products were purified by preparative HPLC and characterized chromatographically and by proton decoupled 3H NMR.