1-boc Piperazine

1-Boc Piperazine: An Overview

1-Boc-piperazine, also known as tert-butoxycarbonyl piperazine, is an organic compound widely used in organic synthesis, particularly as a protected form of piperazine. The term "Boc" stands for tert-butoxycarbonyl, a protecting group used to shield the nitrogen atom of piperazine during chemical reactions, making 1-Boc-piperazine a crucial intermediate in pharmaceuticals, fine chemicals, and peptide synthesis.

Chemical Structure and Properties

Chemical Name: 1-Boc-piperazine

Molecular Formula: C₉H₁₈N₂O₂

Molecular Weight: 186.25 g/mol

CAS Number: 57260-71-6

Physical Properties:

PropertyDescriptionAppearanceWhite crystalline powder or solidMelting Point40-42°CBoiling Point260°C (decomposes)SolubilitySoluble in organic solvents like ethanol, dichloromethane, and acetoneStabilityStable under normal conditions; reacts with acids or bases to remove Boc group

The structure of 1-Boc-piperazine features a piperazine ring in which one nitrogen is protected by a tert-butoxycarbonyl group (-Boc), making it unreactive during certain reactions where the piperazine core is being modified.

Applications

1-Boc-piperazine is widely used as a key intermediate in chemical synthesis, particularly in:

1. Pharmaceuticals: The Boc group is used to protect the nitrogen atom in piperazine during multi-step organic synthesis. Piperazine derivatives are found in various drug classes, including antihistamines, antipsychotics, and anti-infective agents. The Boc-protected form enables selective reactions on other parts of the molecule without interfering with the piperazine ring.
2. Peptide Synthesis: In peptide chemistry, the Boc group is a common nitrogen-protecting group, which can be removed under acidic conditions (such as treatment with trifluoroacetic acid). This allows for selective deprotection, enabling controlled stepwise peptide bond formation.
3. Organic Synthesis: 1-Boc-piperazine is often employed in the synthesis of complex organic molecules. The presence of the Boc group protects the amine from reacting prematurely, allowing chemists to perform transformations elsewhere in the molecule.