(3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine

Base Information

• Chemical Name: (3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine
• CAS No.: 119193-19-0
• Molecular Formula: C13H19NO
• Molecular Weight: 205.3
• Hs Code.: 2932999099
• European Community (EC) Number: 927-919-8,834-688-6
• DSSTox Substance ID: DTXSID30453444
• Nikkaji Number: J723.269A
• Wikidata: Q72470610
• Mol file: 119193-19-0.mol

Synonyms:119193-19-0;(3R,4R)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE;3-((3R,4R)-3,4-diMethylpiperidin-4-yl)phenol;3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol;(+)-(3R,4R)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE;(3r,4r)-3-(3,4-dimethyl-4-piperidinyl)phenol;MFCD06659960;SCHEMBL1477254;DTXSID30453444;HXZDAOSDNCHKFE-GXFFZTMASA-N;PHENOL, 3-[(3R,4R)-3,4-DIMETHYL-4-PIPERIDINYL]-;BCP12721;CS-M1917;AKOS015901845;AKOS016015268;AS-37611;LY-272922;AM20120622;D5558;A848633;(3R pound not4R)-3 pound not4-Dimethyl-4-(3-hydroxyphenyl)piperidine

Chemical Property of (3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine

Chemical Property:

• Appearance/Colour: white like or light brown crystalline powder
• Vapor Pressure: 6.14E-05mmHg at 25°C
• Melting Point: 174-175 °C
• Refractive Index: 1.521
• Boiling Point: 335.464 °C at 760 mmHg
• PKA: 9.85±0.10(Predicted)
• Flash Point: 115.716 °C
• PSA: 32.26000
• Density: 1.009 g/cm³
• LogP: 2.60810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 205.146664230
• Heavy Atom Count: 15
• Complexity: 219

Purity/Quality:

98% ^*data from raw suppliers

3-[(3R,4R)-3,4-Dimethylpiperidin-4-yl]phenol >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNCCC1(C)C2=CC(=CC=C2)O
• Isomeric SMILES: C[C@H]1CNCC[C@@]1(C)C2=CC(=CC=C2)O
• Uses: (3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine is an intermediate in the preparation of Alvimopan (A575800).

Technology Process of (3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine

There total 26 articles about (3R,4R)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine 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: 88.0%

(3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester (145678-86-0) → 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0)

Guidance literature:

With hydrogen bromide; In acetic acid; Reflux;

DOI:10.13005/ojc/340246

Reference yield:

C20H23NO3 → 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0)

Guidance literature:

C₂₀H₂₃NO₃; With hydrogen bromide; acetic acid; for 18h; Heating / reflux;

With sodium hydroxide; water; at 10 - 30 ℃; for 1h; pH=1.7;

Reference yield:

C9H16NO3SBr (951240-63-4) → 3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2.1: CuBr*SMe₂ / tetrahydrofuran; diethyl ether / -40 - -35 °C

3.1: sodium carbonate / Pd(Ph₃P)4 / ethanol; toluene; H₂O / 0.75 h / 80 °C

4.1: anisole; triflic acid / CH₂Cl₂ / 0.5 h / 0 °C

5.1: sodium cyanoborohydride / acetonitrile; H₂O / 0.5 h

6.1: n-butyllithium / tetrahydrofuran / -15 °C

6.2: tetrahydrofuran / -50 °C

7.1: sodium borohydride / methanol

8.1: phenyl chloroformate / toluene

9.1: hydrogen bromide; acetic acid / Heating

With dmap; sodium tetrahydroborate; n-butyllithium; copper(I) bromide dimethylsulfide complex; trifluorormethanesulfonic acid; hydrogen bromide; sodium cyanoborohydride; sodium carbonate; acetic acid; methoxybenzene; triethylamine; phenyl chloroformate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; 2.1: Grignard reaction / 3.1: Suzuki coupling;

DOI:10.1021/ol0713988

upstream raw materials:

(3R,4R)-4-(3-methoxyphenyl)-3,4-dimethylpiperidine

(3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester

C₉H₁₆NO₃SBr

C₁₃H₂₅NO₆SBrP

Downstream raw materials:

methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate

4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-1-tert-butyloxycarbonylpiperidine

1-(3'-oxo-1'-cyclohexenyl)-(3R,4R)-dimethyl-(3-hydroxyphenyl)piperidine

1-(3'-oxo-1'-cyclopentenyl)-(3R,4R)-dimethyl-(3-hydroxyphenyl)piperidine

Refernces

• 1、 Furkert, Daniel P.,Husbands, Stephen M.. "First asymmetrie synthesis of frans-3,4-dimethyl-4-arylpiperidines". . p. 3769 - 3771. Retrieved 2008/02/14.
• 2、 -. "Compositions containing opioid antagonists". Page/Page column 17; 20-21. . Retrieved 2010/11/26.