Benzyl 4-methylidenepiperidine-1-carboxylate

Name: Benzyl 4-methylidenepiperidine-1-carboxylate
Brand: ChemScene
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CAS No. 138163-12-9
Cat. No. CS-0036611
Purity≥95%
MDL No.None

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Benzyl 4-methylidenepiperidine-1-carboxylate|CS-0036611

Structure of 138163-12-9

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General Information

CAS No. 138163-12-9
Cat. No. CS-0036611
Purity ≥95%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₇NO₂
Molecular Weight 231.29
Synonym(s) Benzyl 4-methylenepiperidine-1-carboxylate
SMILES C=C1CCN(CC1)C(=O)OCC2=CC=CC=C2

Description

Benzyl 4-methylidenepiperidine-1-carboxylate features a conjugated enolizable exocyclic double bond at the 4-position, enabling facile Michael additions and Diels–Alder cycloadditions. The benzyl ester group provides stable storage and convenient deprotection under mild hydrogenolysis conditions. This scaffold integrates readily into complex alkaloid syntheses and functionalized heterocycles.

Application

Benzyl 4-methylidenepiperidine-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to piperidine-based scaffolds. The methylidene group facilitates selective functionalization and acts as a key handle for ring expansion or cycloaddition reactions. Its benzyl ester moiety offers excellent bench stability and straightforward deprotection under standard hydrogenolysis conditions, making it ideal for iterative synthesis and late-stage modifications in medicinal chemistry workflows.

Synthesis

Route1
- 19099-93-5
- 1779-49-3
- ~99%
- In-stock
  
  138163-12-9
References
- PFIZER PRODUCTS INC. Patent: WO2008/84300 A1, 2008 ; Location in patent: Page/Page column 74 ; WO 2008/084300 A1
Route2
- 19099-93-5
- ~%
- In-stock
  
  138163-12-9
References
- EP1619193 A1, ; Page/Page column 60-61 ; EP 1619193 A1

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 29.54
LogP 2.9752
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Benzyl 4-methylidenepiperidine-1-carboxylate

CAS No. 138163-12-9

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