37586-22-4

Basic information

• Product Name: 4-BENZOYLPIPERIDINE HYDROCHLORIDE
• Synonyms: 4-BENZOYL PIPERIDINE HCL;TIMTEC-BB SBB003319;PHENYL-PIPERIDIN-4-YL-METHANONE HYDROCHLORIDE;PHENYL(4-PIPERIDINYL)METHANONE;PHENYL(4-PIPERIDYL)METHANONE HYDROCHLORIDE;4-BENZOYLPIPERIDINE;phenyl(4-piperidyl)methanone;Methanone, phenyl-4-piperidinyl-
• CAS NO: 37586-22-4
• Molecular Formula: C₁₂H₁₅NO
• Molecular Weight: 225.71
• Product Categories: Neurochemicals
• Mol File: 37586-22-4.mol

Chemical Properties

• Melting Point: 226 °C
• Boiling Point: 221-224°C
• Flash Point: 125.3 °C
• Appearance: White solid
• Density: 1.054 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(37586-22-4)
• EPA Substance Registry System: 4-BENZOYLPIPERIDINE HYDROCHLORIDE(37586-22-4)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 37586-22-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1S/C12H15NO/c14-12(10-4-2-1-3-5-10)11-6-8-13-9-7-11/h1-5,11,13H,6-9H2

Upstream product

• 25519-79-3 1-(4-benzoylpiperidin-1-yl)ethanone 
• 109555-51-3 1-benzoyl-4-benzoylpiperidine 
• 190142-48-4 4-piperidinylcarbonyl chloride 
• 71-43-2 benzene 
• 31252-42-3 4-benzylpyperidine 

Downstream Products

• 117022-85-2 1-{4-[3-(4-benzoyl-piperidin-1-yl)-propoxy]-3-methoxy-phenyl}-ethanone 
• 141620-44-2 (1-Oxiranylmethyl-piperidin-4-yl)-phenyl-methanone 
• 139676-51-0 4-benzoyl-1-(2-hydroxyethyl)piperidine 
• 114399-88-1 α,α-diphenyl-1-(phenylmethyl)-4-piperidinemethanol 
• 202124-80-9 1-(4-Benzoylpiperidinecarbonyl)methyl-5-cyanoindole 
• 1027540-75-5 [2-(4-benzoyl-piperidin-1-yl)-2-oxo-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 92040-00-1 (1-methylpiperidin-4-yl)(phenyl)methanone 
• 193217-39-9 1-(t-butoxycarbonyl)-4-(benzoyl)piperidine 
• 38081-60-6 phenyl-piperidin-4-yl-methanol 
• 109555-51-3 1-benzoyl-4-benzoylpiperidine 
• 922504-26-5 phenyl(1-tosylpiperidin-4-yl)methanone 
• 916976-31-3 4-benzhydrylidene-1-methanesulfonyl-piperidine 

Relevant articles and documents

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Monoacylglycerol lipase (MAGL) is the enzyme degrading the endocannabinoid 2-arachidonoylglycerol, and it is involved in several physiological and pathological processes. The therapeutic potential of MAGL is linked to several diseases, including cancer. The development of MAGL inhibitors has been greatly limited by the side effects associated with the prolonged MAGL inactivation. Importantly, it could be preferable to use reversible MAGL inhibitors in vivo, but nowadays only few reversible compounds have been developed. In the present study, structural optimization of a previously developed class of MAGL inhibitors led to the identification of compound 23, which proved to be a very potent reversible MAGL inhibitor (IC50 = 80 nM), selective for MAGL over the other main components of the endocannabinoid system, endowed of a promising antiproliferative activity in a series of cancer cell lines and able to block MAGL both in cell-based as well as in vivo assays.

Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.

PIPERIDINE UREA DERIVATIVES

Compounds of the formula I in which R1-R3 have the meanings indicated in Claim 1, are inhibitors of Tankyrase, and can be employed, inter alia, for the treatment of diseases such as cancer, cardiovascular diseases, central nervous system injury and different forms of inflammation.

Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors

A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain.

Synthesis and in vitro and in vivo evaluation of18F-labeled positron emission tomography (PET) ligands for imaging the vesicular acetylcholine transporter

A new class of vesicular acetylcholine transporter inhibitor that incorporates a carbonyl group into the benzovesamicol structure was synthesized, and analogues were evaluated in vitro. (±)-trans-2-Hydroxy-3- (4-(4-[18F]fluorobenzoyl)piperidino)tetralin (9e) has Ki values of 2.70 nM for VAChT, 191 nM for σ1 and 251 nM for σ2. The racemic precursor (9d) was resolved via chiral HPLC, and (±)-[18F]9e,(-)-[18F]9e, and (+)-[ 18F]9e were respectively radiolabeled via microwave irradiation of the appropriate precursors with [18F]/F- and Kryptofix/K 2CO3 in DMSO with radiochemical yields of ～50-60% and specific activities of >2000 mCi/μmol. (-)-[18F]9e uptake in rat brain was consistent with in vivo selectivity for the VAChT with an initial uptake of 0.911 %ID/g in rat striatum and a striatum/cerebellum ratio of 1.88 at 30 min postinjection (p.i.). MicroPET imaging of macaques demonstrated a 2.1 ratio of (-)-[18F]9e in putamen versus cerebellum at 2 h p.i. (-)-[18F]9e has potential to be a PET tracer for clinical imaging of the VAChT.

Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters

In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT 1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [(-)-15b, (-)-15j, (-)-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.

N-substituted alpha-arylazacycloalkylmethanamines and their use as cardiovascular agents

Novel compounds of the formula below wherein W is azetidine, pyrrolidine or piperidine, Q is a straight chain hydrocarbon radical of 1-4 carbons and may contain a double bond, and STR1 Ar is phenyl, pyridinyl or pyrimidinyl, a process for their preparation, and novel intermediates are disclosed. The novel compounds and the pharmaceutical compositions of this invention are useful in the treatment of hypertension, arrhythmias and angina.