1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

Base Information

• Chemical Name: 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine
• CAS No.: 60232-85-1
• Molecular Formula: C17H25 N O
• Molecular Weight: 259.392
• NSC Number: 170516
• UNII: AE1041687F
• DSSTox Substance ID: DTXSID10208979
• Nikkaji Number: J390.372I
• Wikidata: Q6120311
• ChEMBL ID: CHEMBL422629
• Mol file: 60232-85-1.mol

Synonyms:1-(1-phenylcyclohexyl)-4-hydroxypiperidine;PCHP

Chemical Property of 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

Chemical Property:

• Vapor Pressure: 3.79E-07mmHg at 25°C
• Melting Point: 116-118 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• Boiling Point: 400.9°C at 760 mmHg
• PKA: 14.86±0.20(Predicted)
• Flash Point: 106.1°C
• PSA: 23.47000
• Density: 1.093g/cm³
• LogP: 3.24060
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 259.193614421
• Heavy Atom Count: 19
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

1-(1-Phenylcyclohexyl)-4-hydroxypiperidine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)(C2=CC=CC=C2)N3CCC(CC3)O
• Uses: 4-Hydroxy Phencyclidine is a major monohydroxy metabolite of Phencyclidine (P295502) that produces PCP-like stimuli.

Technology Process of 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

There total 10 articles about 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine 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: 85.0%

4-hydroxypiperidinocyclohexyl carbonitrile (60756-86-7) + phenylmagnesium bromide → 1-(1-phenylcyclohexyl)-4-hydroxypiperidine (60232-85-1)

Guidance literature:

In tetrahydrofuran; 1.) reflux, 2 h, 2.) 22 deg C;

Reference yield:

bromobenzene (108-86-1,52753-63-6) + 4-hydroxypiperidinocyclohexyl carbonitrile (60756-86-7) + ethylene dibromide (106-93-4) → 1-(1-phenylcyclohexyl)-4-hydroxypiperidine (60232-85-1)

Guidance literature:

With ammonium chloride; iodine; magnesium; In tetrahydrofuran; methanol; chloroform;

Reference yield:

Phencyclidine (77-10-1) → 1-(1-phenylcyclohexyl)-4-hydroxypiperidine (60232-85-1) + 4-Phenyl-4-piperidinocyclohexanol (60756-83-4) + 5-pentanoic acid (77160-83-9) + 3-hydroxy-1-(1-phenylcyclohexyl)piperidine (94852-59-2)

Guidance literature:

With oxygen; ethylene diamine tetraacetic acid tetrasodium salt; iron(II) sulfate; isoascorbic acid; In water; at 37 ℃; for 1h; Yield given. Further byproducts given; sodium phosphate buffer; var. reag.: Fe(III)TPPCl with iodosylxylene, or cumenehydroperoxide or O₂/Zn/AcOH;

DOI:10.1248/cpb.37.1788

upstream raw materials:

bromobenzene

1-(4-Trimethylsilanyloxy-piperidin-1-yl)-cyclohexanecarbonitrile

Phencyclidine

phencyclidine hydrochloride

Downstream raw materials:

Nicotinic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester

1-(1-Phenyl-cyclohexyl)-4-trimethylsilanyloxy-piperidine

1-(1-phenylcyclohexyl)-4-piperidone

Benzoic acid 1-(1-phenyl-cyclohexyl)-piperidin-4-yl ester

Refernces

• 1、 Hufford,Baker,Clark. "Metabolism of phencyclidine by microorganisms". . p. 155 - 158. Retrieved 1981.
• 2、 -. "Phencyclidine and phencyclidine metabolites assay, tracers, immunogens and antibodies". . . Retrieved 2008/06/13.
• 3、 Itzhak, Yossef,Kalir, Asher,Weissman, Ben Avi,Cohen, Sasson. "New Analgesic Drugs Derived from Phencyclidine". . p. 496 - 499. Retrieved 2007/10/02.