88495-55-0

Basic information

• Product Name: (3S)-3-Piperidinecarboxamide
• Synonyms: (3S)-3-Piperidinecarboxamide;(S)-Piperidine-3-carboxylic acid amide;(S)-Piperidine-3-carboxamide
• CAS NO: 88495-55-0
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.18
• Mol File: 88495-55-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 311.7±31.0 °C(Predicted)
• Appearance: /
• Density: 1.060±0.06 g/cm3(Predicted)
• PKA: 16.50±0.20(Predicted)
• CAS DataBase Reference: (3S)-3-Piperidinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-Piperidinecarboxamide(88495-55-0)
• EPA Substance Registry System: (3S)-3-Piperidinecarboxamide(88495-55-0)

Safety Data

• Hazardous Substances Data: 88495-55-0(Hazardous Substances Data)

Usage

General Description

The chemical (3S)-3-Piperidinecarboxamide, also known as N-Acetyl L-piperidine, is an organic compound with the molecular formula C7H13N3O. It is a derivative of piperidine, a heterocyclic amine that is commonly used in the synthesis of pharmaceuticals and other organic compounds. (3S)-3-Piperidinecarboxamide is an amide, meaning it contains a carbonyl group attached to an amine functional group. It is commonly used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds due to its ability to participate in a wide range of chemical reactions, and its relatively low toxicity.

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Relevant articles and documents

Development and Scale-Up of an Asymmetric Synthesis Process for Alogliptin

Alogliptin (1) benzoate is a potent, highly selective inhibitor of serine protease dipeptidyl-peptidase IV, approved by US FDA for the treatment of type 2 diabetes. Herein, we report a more cost-effective process that includes ruthenium-catalyzed asymmetric hydrogenation followed by Hofmann rearrangement of 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (10) to introduce a chiral amino moiety at a late stage. Use of an inexpensive and readily available nicotinamide (6) for a chiral aminopiperidine core and iodobenzene diacetate (PIDA) under mild and specific conditions allowed us to access 1 with excellent total yield and comparable quality to that manufactured by the original process.

Characterization of an enantioselective amidase from Cupriavidus sp. KNK-J915 (FERM BP-10739) useful for enzymatic resolution of racemic 3-piperidinecarboxamide

A novel amidase (CsAM) acting on (R,S)-N-benzyl-3-piperidinecarboxamide was purified from Cupriavidus sp. KNK-J915 (FERM BP-10739) and characterized. The enzyme acts on (R,S)-N-benzyl-3-piperidinecarboxamide S-selectively to yield (R)-N-benzyl-3-piperidinecarboxamide. Analytical gel filtration column chromatography and SDS-PAGE revealed that the enzyme is a tetramer with a subunit of approximately 47 kDa. It has a broad substrate spectrum against nitrogen-containing heterocyclic amides. Its optimal pH and temperature are 8.0-9.0 and 50 °C, respectively. The CsAM gene was cloned and sequenced, and it was found to comprise 1341 bp and encode a polypeptide of 46,388 Da. The deduced amino acid sequence exhibited 78% identity to that of a putative amidase (CnAM) from Cupriavidus necator JMP134. The cultured cells of recombinant Escherichia coli producing CnAM could be used for the S-selective hydrolysis of (R,S)-N-benzyl-3-piperidinecarboxamide but could not be used for the S-selective hydrolysis of (R,S)-3-piperidinecarboxamide because of its very low level of selectivity. In contrast, the cultured cells of recombinant E. coli producing CsAM could hydrolyze both (R,S)-N-benzyl-3-piperidinecarboxamide and (R,S)-3-piperidinecarboxamide with high S-selectivity.