67686-01-5

Basic information

• Product Name: (1-Benzyl-4-piperidyl)methanol
• Synonyms: (1-BENZYLPIPERIDIN-4-YL)METHANOL;1-BENZYL-4-PIPERIDINEMETHANOL;(1-BENZYL-4-PIPERIDINYL)METHANOL;(1-BENZYL-4-PIPERIDYL)METHANOL;1-BENZYL-4-(HYDROXYMETHYL)PIPERIDINE;BUTTPARK 27\04-75;1-Benzyl-4-Piperdinemethanol;1-Benzy-4-HydroxymethylPiperidine
• CAS NO: 67686-01-5
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.3
• Product Categories: pharmacetical;Alcohol Aldehyde & acid series;Piperidine;Heterocyclic Compounds;Non-Chiral heterocyclic compounds
• Mol File: 67686-01-5.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 135-138°C (0.2 mmHg)
• Flash Point: 139.8 °C
• Appearance: /
• Density: 1.056 g/cm³
• Vapor Pressure: 0.00023mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.94±0.10(Predicted)
• CAS DataBase Reference: (1-Benzyl-4-piperidyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Benzyl-4-piperidyl)methanol(67686-01-5)
• EPA Substance Registry System: (1-Benzyl-4-piperidyl)methanol(67686-01-5)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 24/25-45
• HazardClass: IRRITANT
• Hazardous Substances Data: 67686-01-5(Hazardous Substances Data)

Usage

Synthesis

Charge toluene (100 mL) in a round bottom flask along with vitride (26 g, 0.12 mol) in an inert atmosphere. N-Benzyl ethyl isonipecotate (40 g, 0.16 mol) was added slowly in portions to the reaction mass. The mixture was stirred at room temperature for 2 h. After completion of the reaction the mass was quenched with chilled water. Toluene phase was separated and dried over anhydrous sodium sulfate. Toluene was removed under vacuum to get (1-Benzyl-4-piperidyl)methanol( 26.9 g, 82 %).

Chemical Properties

Colorless liquid

InChI:InChI=1/C13H19NO/c15-11-13-6-8-14(9-7-13)10-12-4-2-1-3-5-12/h1-5,13,15H,6-11H2

Upstream product

• 5274-99-7 1-benzoylisonipecotic acid 
• 10315-07-8 N-benzylpiperidine-4-carboxylic acid 
• 32018-56-7 1-benzyl-4-methyl-1 ,2,3,6-tetrahydropyridine 
• 22065-85-6 N-benzyl-4-formylpiperidine 
• 100-39-0 benzyl bromide 
• 498-94-2 isonipecotic acid 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 616897-44-0 2-(1-benzylpiperidin-4-ylidene)malononitrile 
• 1484-13-5 9-vinyl-9H-carbazole 
• 6457-49-4 4-piperidinemethanol 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 895578-02-6 1-benzyl-3-fluoro-4-hydroxymethyl-1,2,5,6-tetrahydropyridine 

Downstream Products

• 304905-21-3 1-[(1-benzylpiperidin-4-yl)carboxymethyl]naphthalene 
• 1160221-47-5 (1-benzylpiperidin-4-yl)methyl 4-nitrophenyl carbonate 
• 120014-07-5 1-benzyl-4-<(5,6-dimethoxy-1-oxoindan-2-ylidenyl)methyl>piperidine 
• 142057-77-0 donepezil hydrochloride 

Relevant articles and documents

In situ silane activation enables catalytic reduction of carboxylic acids

We describe a catalytic system for the conversion of carboxylic acids into alcohols using substoichiometric zinc acetate and N-methyl morpholine, in combination with phenylsilane as the nominal terminal reductant. Reaction monitoring by19F NMR spectroscopy demonstrates that the reaction proceeds by mutual activation of the carboxylic acid and silane through the in situ generation of silyl ester intermediates.

Cobalt-Catalyzed Remote Hydroboration of Alkenyl Amines

We here present a generally applicable cobalt-catalyzed remote hydroboration of alkenyl amines, providing a practical strategy for the preparation of borylamines and aminoalcohols. This method shows broad substrate scope and good functional group tolerance, tolerating a series of alkenyl amines, including alkyl-alkyl amines, alkyl-aryl amines, aryl-aryl amines, and amides. Of note, this protocol is also compatible with a variety of natural products and drug derivatives. Preliminary mechanistic studies suggest that this transformation involves an iterative chain walking and hydroboration sequence.

Synthesis method of N-benzyl-4-piperidine formaldehyde

The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of N-benzyl-4-piperidine formaldehyde. According to the invention, 4-piperidinecarboxylic acid is used as a raw material; an esterification reaction is carried out to generate 4-methyl piperidinecarboxylate hydrochloride; an alkylation reaction is carried out on N-benzyl-4-methyl piperidinecarboxylate hydrochloride to generate N-benzyl-4-methyl piperidinecarboxylate; n-benzyl-4-methyl piperidinecarboxylate is hydrolyzed to obtain N-benzyl-4-piperidinecarboxylic acid, N-benzyl-4-piperidinecarboxylic acid is subjected to an acylation reaction to generate N-benzyl-4-piperidinecarboxamide, N-benzyl-4-piperidinecarboxamide is dehydrated to obtain 1-benzylpiperidine-4-nitrile, and 1-benzylpiperidine-4-nitrile is subjected to a reduction reaction to generate N-benzyl-4-piperidineformaldehyde. The method is mild in reaction condition, simple in aftertreatment and high in yield, N-benzyl-4-piperidinecarboxaldehyde can be obtained at the high yield at the temperature of 0 DEG C, column chromatography is not needed, and repeatability is high.