3554-74-3

Basic information

• Product Name: 3-Hydroxy-1-methylpiperidine
• Synonyms: 1-Methyl-3-hydroxypiperidine;1-methyl-3-piperidino;NM3PPOL;N-METHYL-3-HYDROXY PIPERIDINE;N-METHYL-3-PIPERIDINOL;3-HYDROXY-N-METHYLPIPERIDINE;3-HYDROXY-1-METHYLPIPERIDINE;1-METHYL-3-PIPERIDINOL
• CAS NO: 3554-74-3
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• EINECS: 222-609-2
• Product Categories: Piperidine;API intermediates;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 3554-74-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 76-78 °C11 mm Hg(lit.)
• Flash Point: 158 °F
• Appearance: /
• Density: 0.999 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.312mmHg at 25°C
• Refractive Index: n20/D 1.475
• PKA: 14.95±0.20(Predicted)
• Water Solubility: Fully misicible in water.
• BRN: 103017
• CAS DataBase Reference: 3-Hydroxy-1-methylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-1-methylpiperidine(3554-74-3)
• EPA Substance Registry System: 3-Hydroxy-1-methylpiperidine(3554-74-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-6/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3554-74-3(Hazardous Substances Data)

Usage

Description

3-Hydroxy-1-methylpiperidine is an organic compound with the molecular formula C6H13NO. It is a heterocyclic compound featuring a piperidine ring with a hydroxyl group at the 3rd position and a methyl group at the 1st position. 3-Hydroxy-1-methylpiperidine is known for its versatile chemical properties and is utilized as a building block in the synthesis of various pharmaceuticals and chemical compounds.

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-1-methylpiperidine is used as a reactant for the optimization of the Novobiocin scaffold to produce antitumor agents. It plays a crucial role in the development of cancer treatments by enhancing the effectiveness of existing drugs and potentially leading to the discovery of new therapeutic options.
Used in Chemical Synthesis:
3-Hydroxy-1-methylpiperidine is used as a reactant for the formation of carbamates and N-alkylimidazoles, which are important intermediates in the synthesis of various chemical compounds.
Used in Medicinal Chemistry:
3-Hydroxy-1-methylpiperidine is used as a reactant for the synthesis of pyridine derivatives that act as CDK5 inhibitors. These inhibitors are valuable in the research and development of treatments for neurodegenerative diseases, such as Alzheimer's and Parkinson's.
Used in Neuropharmacology:
3-Hydroxy-1-methylpiperidine is used as a reactant for the synthesis of phenylcarbamate derivatives, which serve as ligands for nicotinic acetylcholine receptors. These ligands are essential in the study of the nervous system and the development of drugs targeting cognitive functions and neurological disorders.
Used in Catalyst Development:
3-Hydroxy-1-methylpiperidine is used as a reactant for the synthesis of amino phosphite ligands. These ligands are vital in the development of catalysts for various chemical reactions, including those in the pharmaceutical and chemical industries.
Used in Chiral Chemistry:
3-Hydroxy-1-methylpiperidine is used as a reactant for the synthesis of Mexiletine enantiomers through nucleophilic aromatic substitution. Mexiletine is a drug used to treat certain types of nerve pain, and the synthesis of its enantiomers is essential for understanding the stereochemistry of drug action and developing more effective treatments.

InChI:InChI=1/C6H13NO/c1-7-4-2-3-6(8)5-7/h6,8H,2-5H2,1H3

Upstream product

• 31034-86-3 3-hydroxy-1-methylpyridin-1-ium bromide 
• 25065-00-3 1-methyl-pyridinium-3-olate 
• 101-26-8 pyridostigmine bromide 
• 50-00-0 formaldehyd 
• 2439-57-8 N-methyl-N-(tetrahydro-2-furanylmethyl)amine 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 109-00-2 3-HYDROXYPYRIDINE 

Downstream Products

• 37963-15-8 diphenylacetic acid-(1-methyl-[3]piperidyl ester) 
• 3321-80-0 (+)-3-MPB 
• 437-37-6 diphenyl-carbamic acid-(1-methyl-[3]piperidyl ester) 
• 7661-78-1 3,4,5-trimethoxy-benzoic acid-(1-methyl-[3]piperidyl ester) 
• 16597-31-2 (±)-3-benzoyloxy-N-methylpiperidine 
• 101114-85-6 4-methoxy-benzoic acid-(1-methyl-[3]piperidyl ester) 
• 30727-33-4 1-methyl-3-(4-nitro-benzoyloxy)-piperidine 
• 6659-33-2 (±)-3-acetoxy-N-methylpiperidine 
• 99176-14-4 1-methyl-3-piperidinyl butyrate 
• 14189-64-1 3-benzhydryloxy-1-methyl-piperidine 
• 102006-25-7 3,4-dimethoxy-benzoic acid-(1-methyl-[3]piperidyl ester) 
• 6659-30-9 3-dimethylcarbamoyloxy-1-methyl-piperidine 
• 90672-79-0 3-[(3,5-Dimethyl-isoxazol-4-yl)-(4-isopropyl-phenyl)-methoxy]-1-methyl-piperidine 
• 91665-62-2 1-Benzo[d]isoxazol-3-yl-cyclohexanecarboxylic acid 1-methyl-piperidin-3-yl ester 

Relevant articles and documents

Nucleophilicity towards a Vinylic Carbon Atom: Rate Constants for the Addition of Amines to the 1-Methyl-4-vinylpyridinium Cation in Aqueous Solution

Second-order rate constants (kNu) have been measured for the addition of 44 primary amines (including five α-effect amines), 28 secondary amines, 19 tertiary amines, ammonia and hydroxide ion to the vinyl group of the 1-methyl-4-vinylpyridinium cation (1) in aqueous solution at 25 deg C (ionic strength 0.1 mol dm-3).Nucleophilic attack is shown to be rate-determining for primary and secondary amines being generally more reactive than primary amines, with secondary amines of the same basicity.After classification of these species in terms of structure, they describe a number of Broensted-type correlations having βnuc in the range 0.35-0.54 for six structural classes of primary amine, βnuc = 0.48 for α-effect amines, and βnuc in the range 0.23-0.34 for four structural classes of secondary amine.Substitution upon the α-carbon atom reduces amine nucleophilicity of both primary and secondary amines.The presence of an unsaturated carbon atom (either sp2- or sp-hybridized) as the β-carbon atom leads to an enhanced reactivity relative to the corresponding β-sp3 species in all cases.Tertiary amines are in general less reactive than other amines of the same basicity.Broensted-type plots for tertiary amines present the appearance of random scatter which is not readily decipherable in terms of structure. β-Hydroxy and β-amino tertiary amines are unusually reactive relative to their basicity.All of these phenomena suggest that protonation of the carbanionic intermediate by a molecule of water is the rate-determining step for the addition of tertiary amines to 1.Rate constants for the attack of primary and secondary amines on 1 are shown to correlate with literature data for a variety of other reactions involving rate-determining nucleophilic attack of amines upon electrophilic carbon.These kNu for primary and secondary amines reacting with 1 are also shown to correlate with Ritchie's N+ parameters for nucleophilic attack at electrophilic sp2-carbon.N+ parameters for amine nucleophiles have not been widely available previously; the parameters that have been available for selected amines are known to be sensitive to the nature of the defining electrophile.The minimal steric hindrance at the electrophilic centre in nucleophilic attack upon 1 suggests that this species is an appropriate electrophile for the definition of N+ parameters for amine nucleophiles; these parameters are evaluated for 70 primary and secondary amines and ammonia and are suggested to provide an appropriate data base for future investigations of the reactivity and selectivity of amine attack upon sp2-carbon electrophiles in aqueous solution.

REDUCTION OF 1-SUBSTITUTED 3-OXIDOPYRIDINIUMS

1-Substituted 3-oxidopyridiniums are smoothly reduced by sodium borohydride in ethanol to give 1-substituted 3-hydroxypiperidines but much less efficiently by lithium aluminum hydride in hot tetrahydrofuran to give mainly, 1-substituted 5-hydroxypiperid-3-eines.

Derivatives of n-methylpiperidine.

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