4-Hydroxynipecotic acid

Base Information

• Chemical Name: 4-Hydroxynipecotic acid
• CAS No.: 71609-37-5
• Molecular Formula: C₆H₁₁NO₃
• Molecular Weight: 145.158
• DSSTox Substance ID: DTXSID40992172
• Nikkaji Number: J670.421B
• Wikidata: Q82982214
• Mol file: 71609-37-5.mol

Synonyms:4-hydroxy-3-piperidinecarboxylic acid;4-hydroxynipecotic acid;4-hydroxynipecotic acid, cis(+-)-isomer

Chemical Property of 4-Hydroxynipecotic acid

Chemical Property:

• Vapor Pressure: 3.72E-06mmHg at 25°C
• Boiling Point: 346°C at 760 mmHg
• PKA: 3.57±0.40(Predicted)
• Flash Point: 163°C
• PSA: 69.56000
• Density: 1.299g/cm³
• LogP: -0.62980
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 145.07389321
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

CIS-4-HYDROXYNIPECOTIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC(C1O)C(=O)O
• Isomeric SMILES: C1CNC[C@H]([C@H]1O)C(=O)O
• Use Description: 4-Hydroxynipecotic acid has several applications in different fields. In the pharmaceutical industry, it is used as a precursor in the synthesis of various drugs, particularly those involved in the treatment of neurological and psychiatric disorders. Its unique chemical structure makes it valuable in the development of medications that target neurotransmitter systems and influence brain function. Additionally, in the field of organic chemistry, this compound can serve as a building block for the creation of complex organic molecules, contributing to advancements in synthetic chemistry and drug discovery. However, its precise role may vary depending on specific research or industrial requirements within each field, highlighting its potential versatility and importance in various scientific endeavors.

Technology Process of 4-Hydroxynipecotic acid

There total 3 articles about 4-Hydroxynipecotic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

(3RS,4SR)-ethyl 1-(ethoxycarbonyl)-4-hydroxypiperidine-3-carboxylate → (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (68464-00-6,71609-37-5,82817-56-9,126150-99-0)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1021/jm00352a012

Reference yield:

4-oxo-piperidine-1,3-dicarboxylic acid diethyl ester (53601-94-8) → (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (68464-00-6,71609-37-5,82817-56-9,126150-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaBH₄ / ethanol / 3 h / Ambient temperature

2: 60 percent / 5M HCl / 2 h / Heating

With hydrogenchloride; sodium tetrahydroborate; In ethanol;

DOI:10.1021/jm00352a012

Reference yield:

→ (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (68464-00-6,71609-37-5,82817-56-9,126150-99-0)

Guidance literature:

Piperidin-hydrochlorid (+-7a);

upstream raw materials:

4-oxo-piperidine-1,3-dicarboxylic acid diethyl ester

Refernces

• 1、 Krogsgaard-Larsen,Thyssen,Schaumburg. "Inhibitors of GABA uptake. Syntheses and 1H NMR spectroscopic investigations of guvacine, (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid, and related compounds". . p. 327 - 334. Retrieved 2007/10/04.