104-58-5

Basic information

• Product Name: 1-Piperidinepropanol
• Synonyms: 1-PIPERIDINEPROPANOL;3-PIPERIDINOPROPAN-1-OL;3-N-PIPERIDINO-1-PROPANOL;AKOS BC-0904;BUTTPARK 75\06-09;1-(3-Hydroxypropyl)piperidine;1-Propanol, 3-piperidino-;3-(1-Piperidino)propanol
• CAS NO: 104-58-5
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.23
• EINECS: 203-216-5
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Piperidines;Building Blocks;C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 104-58-5.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 94-95 °C0.5 mm Hg(lit.)
• Flash Point: 208 °F
• Appearance: /
• Density: 0.944 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00777mmHg at 25°C
• Refractive Index: n20/D 1.4775(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.12±0.10(Predicted)
• CAS DataBase Reference: 1-Piperidinepropanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinepropanol(104-58-5)
• EPA Substance Registry System: 1-Piperidinepropanol(104-58-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TN2414500
• Hazardous Substances Data: 104-58-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 104-58-5 differently. You can refer to the following data:
1. Reactant in: Mitsunobu reaction of intramolecular nitrile oxide-alkene cycloadditions1 Suzuki-coupling2Reactant for synthesis of: Histamine H3 receptor antagonists3 Protein lysine methyltransferase G9a inhibitors4 Serotonin-4 receptors antagonists5 Checkpoint kinase Chk2 inhibitors6
2. 1-Piperidinepropanol is used in preparation of Ionizable Amine lipids for lipid Nanoparticle compounds that deliver Nucleic Acids.

InChI:InChI=1/C8H17NO/c10-8-4-7-9-5-2-1-3-6-9/h10H,1-8H2

Upstream product

• 503-30-0 trimethylene oxide 
• 110-89-4 piperidine 
• 693-03-8 n-butyl magnesium bromide 
• 627-18-9 1-bromo-3-propanol 
• 14446-67-4 N-allylpiperidine 
• 124-38-9 carbon dioxide 
• 5470-02-0 N-propylpiperidine 
• 107-18-6 allyl alcohol 
• 627-32-7 1-iodopropan-3-ol 
• 23573-93-5 methyl 3-(piperidino)propionate 
• 57-57-8 β-Propiolactone 
• 19653-33-9 ethyl piperidine-1-propionate 
• 627-30-5 1-chloro-3-hydroxypropane 
• 20907-32-8 sodium allyloxide 

Downstream Products

• 114381-41-8 diphenyl-acetic acid-(3-piperidino-propyl ester) 
• 69352-94-9 1-phenyl-cyclopentanecarboxylic acid-(3-piperidino-propyl ester) 
• 108369-31-9 3,4,5-trimethoxy-benzoic acid-(3-piperidino-propyl ester) 
• 110531-42-5 3,4,5-trimethoxy-trans-cinnamic acid-(3-piperidino-propyl ester) 

Relevant articles and documents

Mild LIBF4-Promoted Aminolysis of Oxetanes

LiBF4 in acetonitrile efficiently catalyzes the aminolysis of trimethylene oxide and 2-octyl oxetane under mild conditions (r.t. or 80 deg C) to give the corresponding γ-amino alcohols in very good yields.

Formation of 3-hydroxyalkyl carbamates from carbon dioxide, amines and oxetanes

The reactions of carbon dioxide, primary or secondary aliphatic amines and oxetanes at a CO2 pressure of 40 atm at 100-120°C without any catalysts afforded new monocarbamates of 1,3-propanediols, with concomitant formation of amino alcohols from oxetanes and amines.

-

-

Novel indanone derivatives as MAO B/H3R dual-targeting ligands for treatment of Parkinson's disease

The design of multi-targeting ligands was developed in the last decades as an innovative therapeutic concept for Parkinson's disease (PD) and other neurodegenerative disorders. As the monoamine oxidase B (MAO B) and the histamine H3 receptor (H3R) are promising targets for dopaminergic regulation, we synthetized dual-targeting ligands (DTLs) as non-dopaminergic receptor approach for the treatment of PD. Three series of compounds were developed by attaching the H3R pharmacophore to indanone-related MAO B motifs, leading to development of MAO B/H3R DTLs. Among synthesized indanone DTLs, compounds bearing the 2-benzylidene-1-indanone core structure showed MAO B preferring inhibition capabilities along with nanomolar hH3R affinity. Substitution of C5 and C6 position of the 2-benzylidene-1-indanones with lipophilic substituents revealed three promising candidates exhibiting inhibitory potencies for MAO B with IC50 values ranging from 1931 nM to 276 nM and high affinities at hH3R (Ki 50 = 276 nM, hH3R Ki = 6.5 nM) showed highest preference for MAO B over MAO A (SI > 36). Interestingly, IC50 determinations after preincubation of enzyme and DTLs revealed also nanomolar MAO B potency for 3e (MAO B IC50 = 232 nM), a structural isomer of 3f, and 3d (MAO B IC50 = 541 nM), suggesting time-dependent inhibition modes. Reversibility of inhibition for all three compounds were confirmed by dilution studies in excess of substrate. Thus, indanone-substituted derivatives are promising lead structures for the design of MAO B/hH3R DTLs as novel therapeutic approach of PD therapy.

Ether derivatives of 3-piperidinopropan-1-ol as non-imidazole histamine H3 receptor antagonists

A series of aliphatic and aromatic ether derivatives of 3-piperidinopropan-1-ol has been prepared by four different methods. The ethers obtained were evaluated for their affinities at recombinant human histamine H3 receptor, stably expressed in CHO-K1 or HEK 293 cells. All compounds investigated show from moderate to high in vitro affinities in the nanomolar concentration range. Selected compounds were investigated under in vivo conditions after oral administration to mice. Some proved to be highly potent and orally available histamine H3 receptor antagonists. The most potent antagonists in this series have been in vitro the 4-(1,1-dimethylpropyl)phenyl ether 19 (hH3R Ki = 8.4 nM) and in vivo the simple ethyl ether 2 (ED50 = 1.0 mg/kg).

Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation

Alzheime?s disease (AD) is the most prominent neurodegenerative disorder with high medical need. Protein-protein-interactions (PPI) interactions have a critical role in AD where β-amyloid structures (Aβ) build toxic oligomers. Design of disease modifying multi target directed ligand (MTDL) has been performed, which disable PPI on the one hand and on the other hand, act as procognitive antagonists at the histamine H3 receptor (H3R). The synthetized compounds are structurally based on peptidomimetic amino acid-like structures mainly as keto, diketo-, or acyl variations of a piperazine moiety connected to an H3R pharmacophore. Most of them showed low nanomolar affinities at H3R and some with promising affinity to Aβ-monomers. The structure–activity relationships (SAR) described offer new possibilities for MTDL with an optimized profile combining symptomatic and potential causal therapeutic approaches in AD.

QUINAZOLINE DERIVATIVE

Provided are a quinazoline derivative, a pharmaceutical composition containing the same, a method for preparation of said derivative, and an application of same as an anti-cancer drug.