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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2191137Generated: November 3, 2026

Piperidine → 1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid

https://huagongshe.com/reaction/2191137

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
ReactantDiisopropylethylamineHCID 81531—
Reactant1-Chloroethyl chloroformateHCID 521305—
Reactant4-Chloro-3-fluorophenolHCID 2724523—
Reactant4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrileHCID 46870889—
Reactant(R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanolHCID 59438191—
SolventMethanolHCID 887—
Product1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acidHCID 16227474—
ProductHCID 59438140HCID 59438140—

Reaction Steps

In analogy to the procedure described for the synthesis of 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carbonitrile (example 49) the respective piperidine derivative was prepared from (R)-1-[(3S,4S)-1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol and 4-Chloro-3-fluoro-phenol via Mitsunobu reaction and subsequently the benzyl group was cleaved by treatment with 1-chloroethyl-chloroformate, DIPEA and methanol. Coupling with 5′-Cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (commercially available) yielded the title compound as viscous yellow oil. MS (m/e): 581.5 [(M+H)+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08324248B2
Source datasetuspto-grants-2012_12
ORD IDord-54669182e7ba4e7ebb97b49cd4b639d8
Source noteuspto-grants-2012_12