6152-82-5

Basic information

• Product Name: (R)-1-(2-piperidyl)acetone hydrochloride
• Synonyms: (R)-1-(2-piperidyl)acetone hydrochloride
• CAS NO: 6152-82-5
• Molecular Formula: C₈H₁₅NO*ClH
• Molecular Weight: 177.67174
• EINECS: 228-167-7
• Mol File: 6152-82-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 195°C at 760 mmHg
• Flash Point: 74.3°C
• Appearance: /
• Vapor Pressure: 0.429mmHg at 25°C
• CAS DataBase Reference: (R)-1-(2-piperidyl)acetone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(2-piperidyl)acetone hydrochloride(6152-82-5)
• EPA Substance Registry System: (R)-1-(2-piperidyl)acetone hydrochloride(6152-82-5)

Safety Data

• Hazardous Substances Data: 6152-82-5(Hazardous Substances Data)

Usage

General Description

"(R)-1-(2-piperidyl)acetone hydrochloride" is a chemical compound that is used in the synthesis of various pharmaceuticals and organic compounds. It is classified as an acetylcholinesterase inhibitor, which means it can prevent the breakdown of the neurotransmitter acetylcholine in the brain. This property makes it potentially useful in the treatment of conditions such as Alzheimer's disease and myasthenia gravis. Additionally, the compound has been investigated for its potential as a precursor in the synthesis of other organic compounds. However, as with any chemical, proper safety precautions should be taken when handling and using (R)-1-(2-piperidyl)acetone hydrochloride.

InChI:InChI=1/C8H15NO.ClH/c1-7(10)6-8-4-2-3-5-9-8;/h8-9H,2-6H2,1H3;1H/t8-;/m1./s1

Upstream product

• 1191-30-6 5-bromopentanal 
• 182343-60-8 2-(2-propenyl)-1-piperidinecarboxylic acid tert-butyl ester 
• 1202039-12-0 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid tert-butylester 

Relevant articles and documents

Stereoselective Coupling of N-tert-Butanesulfinyl Aldimines and β-Keto Acids: Access to β-Amino Ketones

The reaction of chiral N-tert-butanesulfinyl aldimines with β-keto acids under basic conditions at room temperature proceeds with high levels of diastereocontrol, leading to β-amino ketones in high yields. Based on DFT calculations, an eight-membered cyclic transition state involving coordination of the lithium atom to the oxygens of carboxylate and sulfinyl units was proposed, being in agreement with the observed experimental diastereomeric ratios. The synthesis of the piperidine alkaloid (-)-pelletierine was successfully undertaken in order to demonstrate the utility of this methodology.

Regioselective and stereoselective copper(I)-Promoted allylation and conjugate addition of N -Boc-2-lithiopyrrolidine and N -Boc-2-lithiopiperidine

Copper salts have been screened for transmetalation and electrophilic quench of N-tert-butoxycarbonyl-2-lithiopyrrolidine (N-Boc-2-lithiopyrrolidine) and N-Boc-2-lithiopiperidine, formed by deprotonation of N-Boc-pyrrolidine and N-Boc-piperidine, respectively. Transmetalation with zinc chloride then (lithium chloride solubilized) copper cyanide followed by allylation typically gives mixtures of regioisomers (SN2 and SN2′ products), whereas transmetalation with copper iodideTMEDA then allylation occurs regioselectively (SN2 mechanism). Addition to an enone or α,β-unsaturated ester occurs by 1,4-addition. Asymmetric deprotonation of N-Boc-pyrrolidine or dynamic resolution in the presence of a chiral ligand of N-Boc-2-lithiopiperidine followed by the zinc/copper chemistry was successful and gave the allylated pyrrolidine and piperidine products with good enantioselectivity, although use of the copper iodide chemistry resulted in some loss of enantiopurity. The chemistry provides formal syntheses of (+)-allosedridine, (+)-lasubine II, and (+)-pseudohygroline and has been used for the synthesis of (+)-coniine, (-)-pelletierine, (+)-coniceine, (-)-norhygrine, and the ant extract alkaloids cis- and trans-2-butyl-5- propylpyrrolidine.