555-92-0

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-2-PROPYLPIPERIDINE HYDROCHLORIDE is used as a pharmaceutical intermediate for the synthesis of various drugs, including antipsychotic and antihistaminic medications, due to its psychoactive properties and ability to contribute to the development of these therapeutic agents.
Used in Chemical Research and Development:
(+/-)-2-PROPYLPIPERIDINE HYDROCHLORIDE is utilized in chemical research and development for the exploration of its potential applications and properties, furthering the understanding of its role in the synthesis of pharmaceutical compounds and its potential for new drug discoveries.

InChI:InChI=1/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/t8-/m1/s1

Upstream product

• 146253-91-0 (S)-4-Chloro-2-propyl-2H-pyridine-1-carboxylic acid benzyl ester 
• 458-88-8 coniine 
• 113965-36-9 (S)-1-((S)-1-Phenyl-ethyl)-2-propyl-piperidine 
• 121675-94-3 (2S)-2-propyl-1-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)piperidine 
• 902121-33-9 (2S)-N-(2',3'4'-tri-O-pivaloyl-α-D-arabinopyranosyl)-2-n-propylpiperidine 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 944128-18-1 (-)-(6S,2S)-1-(2-methoxymethylpyrrolidin-1-yl)-6-propylpiperidin-2-one 
• 214267-24-0 1-((S)-3-Phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-yl)-1H-benzotriazole 
• 5824-74-8 N-methyl-N-(piperidin-1-yl)amine 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 132599-87-2 (6S)-2,3-didehydro-6-n-propylpiperidin-4-one 
• 142764-70-3 N-(benzyloxycarbonyl)-(6S)-6-n-propylpiperidin-4-one 
• 132599-74-7 (S)-3-Methyl-2-((S)-4-oxo-2-propyl-3,4-dihydro-2H-pyridin-1-yl)-pentanoic acid methyl ester 
• 108-55-4 glutaric anhydride, 

Relevant academic research and scientific papers

Enantioselective Rhodium-Catalyzed Allylation of Aliphatic Imines: Synthesis of Chiral C Aliphatic Homoallylic Amines

Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.

Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Allenes

The rhodium-catalyzed asymmetric intramolecular hydroamination of sulfonyl amides with terminal allenes is reported. It provides selective access to 5- and 6-membered N-heterocycles, scaffolds found in a large range of different bioactive compounds. Moreover, gram scale reactions, as well as the application of suitable product transformations to natural products and key intermediates thereof are demonstrated.

Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

We have succeeded in accomplishing the deracemization of (±)-2-acetoxydecyl and (±)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-γ-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate.

A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.

Straightforward access to enantioenriched 2-allylpiperidine: Application to the synthesis of alkaloids

An efficient stereocontrolled preparation of (2R,RS)-2-allyl-(N- tert-butylsulfinyl)piperidine and its enantiomer is detailed. The sequence requires only two synthetic operations with one-column chromatography and is readily scaled up. The versatility of these chiral building blocks was exemplified by the total or formal synthesis of some natural and unnatural alkaloids.

Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

The conjugate addition of an enantiopure lithium amide to a ζ-hydroxy-α,β-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-δ-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C).

Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate

The stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine and (+)-sedamine has been achieved through a common intermediate generated from butane-1,4-diol. The synthetic sequence involves a Maruoka asymmetric allylation and ring-closing metathesis as the key steps.

Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines

A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF 6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.

Asymmetric synthesis of piperidines and octahydroindolizines

The conjugate addition of a homochiral lithium amide to a ξ-hydroxy-α,β-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-δ-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A. Georg Thieme Verlag Stuttgart.

Asymmetrie synthesis of unsaturated monocyclic and bicyclic nitrogen heterocycles

Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R) CHCH2 and allylatlon, or acylatlon with but-3-enoic acid, followed by ring-closing metathesis resulted In the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anlsomycln (R = p-MeOC 6H4). Extension of this methodology with R = CH 2CHCH2 employing two ring-closing metatheses resulted In the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.