3608-67-1

Basic information

• Product Name: 1-methyl-4-piperidyl diphenylglycolate
• Synonyms: 1-methyl-4-piperidyl diphenylglycolate;enpiperate;2-Hydroxy-2,2-diphenylacetic acid 1-methyl-4-piperidinyl ester;Hydroxydiphenylacetic acid 1-methyl-4-piperidyl ester;N-Methyl-4-piperidyl benzilate;α-Hydroxy-α-phenylbenzeneacetic acid 1-methyl-4-piperidinyl ester;Hydroxy-diphenyl-acetic acid 1-Methyl-piperidin-4-yl ester;1-Methylpiperidin-4-yl 2-hydroxy-2,2-diphenylacetate
• CAS NO: 3608-67-1
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.40152
• EINECS: 222-774-0
• Mol File: 3608-67-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 161-162 °C
• Boiling Point: 415.9°Cat760mmHg
• Flash Point: 205.3°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 1.16E-07mmHg at 25°C
• Refractive Index: 1.61
• PKA: 11.29±0.29(Predicted)
• CAS DataBase Reference: 1-methyl-4-piperidyl diphenylglycolate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-4-piperidyl diphenylglycolate(3608-67-1)
• EPA Substance Registry System: 1-methyl-4-piperidyl diphenylglycolate(3608-67-1)

Safety Data

• Hazardous Substances Data: 3608-67-1(Hazardous Substances Data)

Usage

General Description

1-methyl-4-piperidyl diphenylglycolate is a chemical compound that belongs to the class of piperidine derivatives. It is also known by its trade name, "Diphenylglycoluril." 1-methyl-4-piperidyl diphenylglycolate is commonly used as an antispasmodic agent and is often found in pharmaceutical formulations for its muscle relaxant properties. It works by blocking the action of acetylcholine at muscarinic receptors in smooth muscle, leading to a reduction in muscle contractions and spasticity. Additionally, it has been investigated for its potential use in the treatment of Parkinson's disease. Overall, 1-methyl-4-piperidyl diphenylglycolate has therapeutic applications in the management of various conditions related to muscle spasms and motor function.

InChI:InChI=1/C20H23NO3/c1-21-14-12-18(13-15-21)24-19(22)20(23,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18,23H,12-15H2,1H3

Upstream product

• 106-52-5 N-methyl-4-hydroxypiperidine 
• 52182-15-7 ethyl benzilate 
• 80154-05-8 1-methylpiperidin-4-ol monohydrochloride 
• 2902-98-9 2-chloro-2,2-diphenylacetyl chloride 
• 74-83-9 methyl bromide 
• 64749-86-6 3-benziloyloxy-1-(2,2-dimethyl-1,3-dioxolan-4ylmethyl)piperidine 
• 60569-19-9 propiverine 
• 54556-98-8 propiverine hydrochloride 
• 76-89-1 methyl benzilate 
• 76-93-7 Benzilic acid 

Downstream Products

• 5634-41-3 4-benziloyloxy-1,1-dimethyl-piperidinium; bromide 
• 38528-48-2 hydroxy-DAMP 
• 91614-25-4 trans 4-benziloyloxy-1-trideuteriomethyl-1-methylpiperidinium bromide 
• 91614-26-5 cis 4-benziloyloxy-1-trideuteriomethyl-1-methylpiperidinium bromide 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 76-93-7 Benzilic acid 
• 118108-69-3 Benzilsaeure(1-methylpiperid-4-yl)ester-N-oxide 
• 118108-70-6 Benzilsaeure(1-methylpiperid-4-yl)ester-N-oxide 
• 55190-56-2 3-hydroxy-3-phenylbenzo-2(3H)-furanone 
• 117-99-7 2-Hydroxybenzophenone 
• 107411-17-6 4-Hydroxy-benzilsaeure 
• 1137-42-4 4-Hydroxybenzophenone 
• 25811-48-7 2,2-diphenyl-2-hydroxyacetic acid (piperidine-4-yl) ester 
• 111051-49-1 1-methyl-4-piperidyl benzilate N-oxide 

Relevant articles and documents

NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS

The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.

Synthesis, antimuscarinic activity and quantitative structure-activity relationship (QSAR) of tropinyl and piperidinyl esters

A series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log k(w), size (molecular volume) and electronic character (Taft's polar substituent constant δ and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.

Biomimetic oxidation of propiverinhydrochloride and 1-methyl-4-piperidyl benzilate

The reaction of propiverinhydrochloride (1) and 1-methyl-4-piperidyl benzilate (2) with the biomimetic system manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride (MnTPFPPCl)/pyridine/hydrogen peroxide affords unchanged 1 and 2 and 15 potential metabolites, which were isolated and identified. These compounds are products of cleavage of the ester bond, of O-dealkylation, aromatic oxidation, respectively of decarboxylation, demethylation, and N-oxidation. Products were identified by TLC, UV, and MS in comparison with authentic samples. Thereby we found a nearly conformity with rat metabolism.