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 
• 498-94-2 isonipecotic acid 
• 7732-18-5 water 
• 584-08-7 potassium carbonate 
• 100-44-7 benzyl chloride 
• 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 
• 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 
• 100-52-7 benzaldehyde 

Downstream Products

• 304905-21-3 1-[(1-benzylpiperidin-4-yl)carboxymethyl]naphthalene 
• 120014-06-4 donepezil 
• 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.

Synthesis and Bio-Evaluation of N-Benzylpiperidine-8-Hydroxyquinoline Derivatives as Potential Cholinesterase Inhibitors, Metal Ion Chelators and Calcium Channel Blockers

Abstract: A new series of N-benzylpiperidine 8-hydroxyquinoline derivatives were synthesized and evaluated as cholinesterase inhibitors, metal ion chelators and calcium channel blockers. It was found that the ethyl cholinesterase inhibition activity could be improved when the linker between N-benzylpiperidine and 8?hydroxyquinoline groups were extended. Among all derivatives, compound (XIIId) showed best acetyl cholinesterase inhibition activity with an IC50 value of 0.24 ± 0.03 μM. It also showed metal ion chelating activity with a metal-compound ratio of 1 : 2 on copper or zinc ions. The calcium channel blocking property of select compounds were tested and compared by patching clamp on HEK293 cell expressing Cav1.2 calcium channel. Among tested compounds, cholinesterase inhibitor 8c showed mild calcium channel blockade activity with the inhibition ratio of calcium channel of 24.56 ± 2.44% (10 μM). This result suggested that the potential neuroprotective ability of this cholinesterase inhibitor might be partially related to the calcium channel blocking property.

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.