Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)

Nisar Ullah; Ali Ahmed Qaid Al-Shaheri

doi:10.1515/znb-2012-0312

Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)

Nisar Ullah^*
, Ali Ahmed Qaid Al-Shaheri

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

A series of new 4-aryl-1-(biarylmethylene)piperidines have been synthesized. They are structurally related to SLV-313, a potential atypical antipsychotic agent with potent D₂ receptor antagonist and 5-HT _1A receptor agonist properties. Suzuki-Miyaura reaction of cyclic vinyl boronates, derived from the vinyl triflates of N-protected tetrahydropyridines, with appropriate aryl halides yielded 4-arylpiperidines. The reductive amination of the latter with suitable biarylaldehdyes accomplished the synthesis of the new compounds.

Original language	English
Pages (from-to)	253-262
Number of pages	10
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	67
Issue number	3
DOIs	https://doi.org/10.1515/znb-2012-0312
State	Published - Mar 2012

Bibliographical note

Funding Information:
The financial support from KACST Project No: AR-28-38 and lab facilities from KFUPM are gratefully acknowledged.

Keywords

Aryl-(biarylmethylene)piperidines
Reductive amination
Schizophrenia
Suzuki-Miyaura reaction

ASJC Scopus subject areas

General Chemistry

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10.1515/znb-2012-0312

Cite this

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title = "Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)",

abstract = "A series of new 4-aryl-1-(biarylmethylene)piperidines have been synthesized. They are structurally related to SLV-313, a potential atypical antipsychotic agent with potent D2 receptor antagonist and 5-HT 1A receptor agonist properties. Suzuki-Miyaura reaction of cyclic vinyl boronates, derived from the vinyl triflates of N-protected tetrahydropyridines, with appropriate aryl halides yielded 4-arylpiperidines. The reductive amination of the latter with suitable biarylaldehdyes accomplished the synthesis of the new compounds.",

keywords = "Aryl-(biarylmethylene)piperidines, Reductive amination, Schizophrenia, Suzuki-Miyaura reaction",

author = "Nisar Ullah and Al-Shaheri, \{Ali Ahmed Qaid\}",

note = "Funding Information: The financial support from KACST Project No: AR-28-38 and lab facilities from KFUPM are gratefully acknowledged.",

year = "2012",

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doi = "10.1515/znb-2012-0312",

language = "English",

volume = "67",

pages = "253--262",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

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AU - Ullah, Nisar

AU - Al-Shaheri, Ali Ahmed Qaid

N1 - Funding Information: The financial support from KACST Project No: AR-28-38 and lab facilities from KFUPM are gratefully acknowledged.

PY - 2012/3

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AB - A series of new 4-aryl-1-(biarylmethylene)piperidines have been synthesized. They are structurally related to SLV-313, a potential atypical antipsychotic agent with potent D2 receptor antagonist and 5-HT 1A receptor agonist properties. Suzuki-Miyaura reaction of cyclic vinyl boronates, derived from the vinyl triflates of N-protected tetrahydropyridines, with appropriate aryl halides yielded 4-arylpiperidines. The reductive amination of the latter with suitable biarylaldehdyes accomplished the synthesis of the new compounds.

KW - Aryl-(biarylmethylene)piperidines

KW - Reductive amination

KW - Schizophrenia

KW - Suzuki-Miyaura reaction

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DO - 10.1515/znb-2012-0312

M3 - Article

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SN - 0932-0776

VL - 67

SP - 253

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JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 3

ER -

Synthesis of new 4-aryl-1-(biarylmethylene)piperidines. Structural analogs of adoprazine (SLV313)

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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