50541-93-0

Basic information

• Product Name: 4-Amino-1-benzylpiperidine
• Synonyms: 1-(Phenylmethyl)-4-piperidinamine, Base Form;N-benzyl-4-piperidylamine;1-benzyl-4-piperidylamine;4-AMINO-1-BENZYLPIPERIDINE, 98+%;4-AMINO-N-BENZYL PIPERIDONE;4-Piperidinamine, 1-(phenylmethyl)-;4-Amino-1-benzylpiperidine 98%;1-(Phenylmethyl)piperidin-4-amine
• CAS NO: 50541-93-0
• Molecular Formula: C₁₂H₁₈N₂
• Molecular Weight: 190.28472
• EINECS: 256-620-9
• Product Categories: PHARMACEUTICAL INTERMEDIATES;Piperidines, Piperidones, Piperazines;Piperidine;Amines;Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 50541-93-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 121-122 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 152 °C (9.7 mmHg)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.933 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000794mmHg at 25°C
• Refractive Index: n20/D 1.543(lit.)
• Storage Temp.: 2-8°C
• Solubility: 10g/l
• PKA: 10.15±0.20(Predicted)
• Water Solubility: immiscible
• Sensitive: Air Sensitive
• BRN: 146038
• CAS DataBase Reference: 4-Amino-1-benzylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1-benzylpiperidine(50541-93-0)
• EPA Substance Registry System: 4-Amino-1-benzylpiperidine(50541-93-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10-34
• HazardClass: IRRITANT
• Hazardous Substances Data: 50541-93-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light yellow liquid

Uses

4-Amino-1-benzylpiperidine was used in the preparation of:butyl 4-amino-1-piperidineacetate, key intermediate required for the synthesis of butyl 4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidineacetate5-alkylimino-1,2,4-thiadiazolidine-3-ones, such as 4-ethyl-5-[imino-[1-(phenylmethyl)-4-piperidinyl]]-2-methyl-1,2,4-thiadiazolidin-3-one and 4-benzyl-5-[imino-[1-(phenylmethyl)-4-piperidinyl]]-2-isopropyl-1,2,4-thiadiazolidin-3-oneglycyrrhetinic acid derivatives

Purification Methods

Purify it by distillation in vacuo and store it under N2 because it absorbs CO2. The dihydrochloride salt [1205-72-7] has m 270-273o (255o) after recrystallisation from MeOH/EtOAc or EtOH. [Brookes J Chem Soc 3165, 3172 1957.] The 4-methylamino-1-benzylpiperidine derivative has b 168-172o/17mm, nD 1.5367 [Reitsema & Hunter J Am Chem Soc 70 4009 1948]. The 1-(1-benzyl-4-piperidinyl)-3-cyano-2-methylisothiourea derivative has m 160o from CHCl3/Et2O [Preparation, IR, NMR: Ried et al. Chem Ber 116 1547 1983, Beilstein 22 III/IV 3752].

InChI:InChI=1/C12H18N2/c1-2-4-11(5-3-1)10-14-12-6-8-13-9-7-12/h1-5,12-14H,6-10H2

Upstream product

• 949-69-9 N-benzyl-4-(N-hydroxyimino)piperidine 
• 35621-01-3 4-aminopiperidine dihydrochloride 
• 100-44-7 benzyl chloride 
• 202198-91-2 N-benzylpiperidin-4-yl-benzylamine 
• 100-52-7 benzaldehyde 
• 41661-47-6 piperidin-4-one 
• 39546-32-2 4-carboxamidopiperidine 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 50534-33-3 2-[1-(Phenylmethyl)-4-piperidinyl]-1H-isoindol-1,3(2H)-dione 
• 100-39-0 benzyl bromide 
• 4727-72-4 1-benzyl-4-hydroxypiperidine 
• 5382-16-1 4-HYDROXYPIPERIDINE 
• 4783-65-7 N-benzyl-2-piperidinone 
• 64-17-5 ethanol 

Downstream Products

• 64168-08-7 1-benzyl-N,N-dimethylpiperidin-4-amine 
• 76167-42-5 1-benzyl-4-(2'-pyrimidylamino)piperidine 
• 79206-95-4 4-(1'-Benzyl-piperidino-4')-thiomorpholin-S-dioxid 
• 165807-04-5 pyridine-4-carboxaldehyde (1-benzylpiperidin-4-yl)imine 
• 79098-92-3 1-benzyl-4-(2-hydroxyphenylmethyl)aminopiperidine 
• 180144-29-0 N-(1-benzylpiperid-4-yl)-N'-tert-butylthiourea 
• 186641-18-9 6-nitro-N-(1-benzyl-4-piperidinyl)-1,2-benzisoxazole-3-carboxamide 
• 1026922-21-3 (1-Benzyl-piperidin-4-yl)-[2-(2-pyrimidin-5-yl-phenoxy)-ethyl]-amine 
• 13035-19-3 4-aminopiperidine 
• 971-34-6 1-benzyl-4-benzamidopiperidine 
• 254115-91-8 1-benzyl-4-(1H-pyrrol-1-yl)piperidine 
• 254115-88-3 1-(1-benzyl-piperidin-4-yl)-1H-pyrrole-3-carbaldehyde 
• 253192-28-8 4-(1-benzyl-piperidin-4-ylamino)-benzoic acid tert-butyl ester 

Relevant articles and documents

An improved scalable process for synthesis of piperidin-4-yl-carbamates

An efficient route for the synthesis of methyl piperidine-4-yl-carbamate para-toluene sulfonate salt has been developed. The synthesis involves the reductive amination of 1-benzylpiperidin-4-one with ammonia using Raney-Ni as a catalyst followed by de-protection of benzyl group and finally by making its salt. The advantage of this methodology includes use of easily available commercial raw materials and shorter reaction times with high yields makes this process most viable for large scale manufacturing methyl piperidine-4-yl-carbamate salts.

Claulansine F-donepezil hybrids as anti-alzheimer’s disease agents with cholinergic, free-radical scavenging, and neuroprotective activities

The multifactorial nature of Alzheimer’s disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A total of 26 Claulansine F-donepezil hybrids were designed and synthesized as multitarget drugs. Among these compounds, six compounds exhibited excellent acetylcholinesterase (AChE) inhibitory activity (half maximal inhibitory concentration (IC50) 1.63-4.62 μM). Moreover, (E)-3-(8-(tert-Butyl)-3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazol- 5-yl)-N-((1-(2-chlorobenzyl)piperidin-4-yl)methyl)acrylamide (6bd) exhibited better neuroprotective effects against OGD/R (oxygen-glucose deprivation/reoxygenation) than lead compound Claulansine F. Furthermore, 6bd could cross the blood-brain barrier in vitro. More importantly, compared to edaravone, 6bd had stronger free-radical scavenging activity. Molecular docking studies revealed that 6bd could interact with the catalytic active site of AChE. All of these outstanding in vitro results indicate 6bd as a leading structure worthy of further investigation.

Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase

In recent years, ALR2 (aldose reductase) inhibitors have attracted attention for their effective ability to reduce the progression of diabetes-associated cataracts. Therefore, in the present article, we intended to develop novel thiazole-sulfonamide hybrids as a potent inhibitor of ALR2. These molecules significantly inhibited the ALR2 level in the rat lenses homogenate, where the most potent compound 7b showed activity comparable to sorbinil as standard. In Wistar rats, compound 7b improved the insulin level and body weight of the experimental animal together with a reduction in the glucose output. Compound 7b showed a significant reduction in the expression of ALR2 in rat lenses in western blot analysis.