5773-58-0

Basic information

• Product Name: 3-METHYL-4-PIPERIDONE
• Synonyms: AKOS BC-0319;3-METHYL-4-PIPERIDONE;3-METHYLPIPERIDIN-4-ONE;4-Piperidinone, 3-Methyl-
• CAS NO: 5773-58-0
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• Product Categories: 11
• Mol File: 5773-58-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 182.631 °C at 760 mmHg
• Flash Point: 81.781 °C
• Appearance: /
• Density: 0.951g/cm³
• Vapor Pressure: 0.803mmHg at 25°C
• Refractive Index: 1.438
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.98±0.40(Predicted)
• CAS DataBase Reference: 3-METHYL-4-PIPERIDONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-4-PIPERIDONE(5773-58-0)
• EPA Substance Registry System: 3-METHYL-4-PIPERIDONE(5773-58-0)

Safety Data

• Hazardous Substances Data: 5773-58-0(Hazardous Substances Data)

Usage

General Description

3-Methyl-4-piperidone, also known as 3,4-lutidine, is a chemical compound with the formula C6H11NO. It is a colorless to pale yellow liquid with a strong odor and is commonly used as a building block in the production of pharmaceuticals, agrochemicals, and other organic compounds. 3-Methyl-4-piperidone is a versatile intermediate in the synthesis of various compounds, including pharmaceuticals, such as anesthetics, analgesics, and antipsychotic drugs. It is also used as a solvent in the manufacture of resins, polymers, and coatings. This chemical is commercially available and is considered to be a valuable building block for the synthesis of a wide range of organic compounds.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.