4593-16-2

Basic information

• Product Name: 1-ACETYL-3-METHYLPIPERIDINE
• Synonyms: 1-ACETYL-3-METHYLPIPERIDINE;1-acetyl-3-methyl-piperidin;1-(3-methyl-1-piperidyl)ethanone;1-(3-methylpiperidin-1-yl)ethanone;1-(3-Methyl-1-piperidinyl)-ethanone;1-Acetyl-3-pipecoline
• CAS NO: 4593-16-2
• Molecular Formula: C₈H₁₅NO
• Molecular Weight: 141.21
• EINECS: 224-983-2
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Piperidines;Building Blocks;C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4593-16-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 239 °C(lit.)
• Flash Point: 224 °F
• Appearance: /
• Density: 0.974 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0406mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• CAS DataBase Reference: 1-ACETYL-3-METHYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-3-METHYLPIPERIDINE(4593-16-2)
• EPA Substance Registry System: 1-ACETYL-3-METHYLPIPERIDINE(4593-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4593-16-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 4593-16-2 differently. You can refer to the following data:
1. Reactant for: Regioselective amidyl radical cyclization1 Regioselective oxidation of cyclic amino compounds2
2. 1-Acetyl-3-methylpiperidine may be employed as piperidine ligand to investigate the enzymatic activity and three-dimensional structure non-peptide ligand-cyclophilin complexes.

InChI:InChI=1/C8H15NO/c1-7-4-3-5-9(6-7)8(2)10/h7H,3-6H2,1-2H3

Upstream product

• 108-24-7 acetic anhydride 
• 626-56-2 3-Methylpiperidine 
• 1039553-34-8 C₁₄H₁₉NOS 
• 75-36-5 acetyl chloride 

Downstream Products

• 1568025-98-8 1-(3-methylpiperidin-1-yl)-3-phenylpropane-1,3-dione 
• 2162-86-9 1-ethyl-3-methyl-piperidine 

Relevant articles and documents

Development of highly regioselective amidyl radical cyclization based on lone pair-lone pair repulsion

(Chemical Equation Presented) The substituent effect on the reactivity and regioselectivity of N-(4-pentenyl)amidyl radical cyclization was investigated. Exclusive 6-endo cyclization was observed for N-(4-pentenyl)amidyl radicals with internal vinylic heteroatom substitution (Cl, Br, I, OMe, SEt). The substituent on the carbonyl group also showed a significant influence on the reactivity of amidyl radicals, which increases in the order of Ph a result, the photostimulated reactions of N-(4-halopent-4-enyl)amides and carbamates (X = Cl, Br, I) with DIB/I2 or Pb(OAc)4/I 2 led to the efficient and exclusive formation of the corresponding piperidines while those of N-(5-halopent-4-enyl)amides afforded the pyrrolidine products only. The halogen-substitution effect also allowed the 6-exo and 7-endo amidyl radical cyclization to proceed in a highly regioselective manner. The above experimental results, in combination with theoretical analyses, revealed that the lone pair-lone pair repulsion between the nitrogen radical and the vinylic heteroatom played an important role in controlling the regioselectivity of cyclization.

NMR Spectra and Stereochemistry of N-Acetyl and N-Benzoyl Derivatives of Solasodine

N-Acetylation of solasodine gives only one rotameric N-acetyl derivative compared with N-acetyl-3-methylpiperidine, which exists in solution as two equally populated rotamers.The 1H and 13C NMR spectra (CDCl3) of O,N-diacetyl- and O-acetyl-N-benzoylsolasodine indicate significant deviations from F-ring chair geometry.Opening of the F ring of these derivatives in CDCl3 solution at 25 deg C, to give the corresponding furosta-5,20(22)-diene derivatives, was ascertained by NMR spectroscopy.Key Words: Solasodine O,N-Diacetylsolasodine O-Acetyl-N-benzoylsolasodine 3β-Acetoxy-26-acetamidofurosta-5,20(22)-diene 3β-Acetoxy-26-benzamidofurosta-5,20(22)-diene