ent-Paroxetine Hydrochloride

Base Information

• Chemical Name: ent-Paroxetine Hydrochloride
• CAS No.: 130855-30-0
• Molecular Formula: C₁₉H₂₀FNO₃*ClH
• Molecular Weight: 365.832
• Hs Code.: 2934990002
• UNII: E8A4U5DP45
• DSSTox Substance ID: DTXSID70595337
• Mol file: 130855-30-0.mol

Synonyms:130855-30-0;ent-Paroxetine Hydrochloride;Paroxetine impurity D;E8A4U5DP45;Paroxetine hydrochloride, (+)-;(+)-trans-Paroxetine Hydrochloride;Paroxetine hydrochloride, trans-(+)-;(3R,4S)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrochloride;(3R,4S)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine hydrochloride;(3R,4S)-3-((Benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine hydrochloride;(3R,4S)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine Hydrochloride ((+)-trans-Paroxetine Hydrochloride);GELRVIPPMNMYGS-SATBOSKTSA-N;UNII-E8A4U5DP45;SCHEMBL6100418;DTXSID70595337;AKOS025401435;AC-16421;DS-018346;EN300-115519;J-005888;Z1489071220;(3R,4S)-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidinehydrochloride;(3R,4S)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine hydrochloride;(3R,4S)-3-[(1,3-dioxaindan-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine hydrochloride;PAROXETINE RELATED COMPOUND C (15 MG) ((+)-TRANS-PAROXETINE HYDROCHLORIDE);trans-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine hydrochloride;trans-3-((Benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidinehydrochloride;(3R,4S)-3-{[(2H-1,3-Benzodioxol-5-yl)oxy]methyl}-4-(4-fluorophenyl)piperidine--hydrogen chloride (1/1)

Chemical Property of ent-Paroxetine Hydrochloride

Chemical Property:

• PSA: 39.72000
• LogP: 4.45730
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 365.1193994
• Heavy Atom Count: 25
• Complexity: 402

Purity/Quality:

98%,99%, ^*data from raw suppliers

ent-Paroxetine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41-62
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC(C1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4.Cl
• Isomeric SMILES: C1CNC[C@@H]([C@H]1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4.Cl
• Uses: An enantiomeric impurity of Paroxetine (P205750). ent-Paroxetine Hydrochloride (Paroxetine EP Impurity D; Paroxetine USP Related Compound C) is an enantiomeric impurity of Paroxetine (P205750).

Technology Process of ent-Paroxetine Hydrochloride

There total 86 articles about ent-Paroxetine Hydrochloride 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: 99.0%

(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine (200572-35-6) → (-)-paroxetine hydrochloride (110429-35-1,130855-30-0)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; at 75 ℃; for 5h;

DOI:10.1021/ja037177o

Reference yield: 97.0%

(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylic acid phenyl ester (253768-88-6) → (-)-paroxetine hydrochloride (110429-35-1,130855-30-0)

Guidance literature:

(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylic acid phenyl ester; With potassium hydroxide; In sulfolane; toluene; at 80 - 85 ℃; for 4h;

With water; In sulfolane; toluene; at 30 - 35 ℃;

With hydrogenchloride; In water; toluene; at 20 - 25 ℃; for 2h; Product distribution / selectivity;

Reference yield: 89.5%

(3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-{[3,4-(methylenedioxy)-phenoxy]methyl}piperidine hydrochloride → (-)-paroxetine hydrochloride (110429-35-1,130855-30-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In isopropyl alcohol; at 40 ℃; for 3h; under 375.03 - 3750.3 Torr;

DOI:10.1002/ejoc.200400067

upstream raw materials:

4-flourophenylmagnesium bromide

Sesamol

4-(4-fluorophenyl)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydropyridine

(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine

Refernces

• 1、 Chamorro-Arenas, Delfino,Fuentes, Lilia,Quintero, Leticia,Cruz-Gregorio, Silvano,H?pfl, Herbert,Sartillo-Piscil, Fernando. "Diastereoconvergent Synthesis of (–)-Paroxetine". . p. 4104 - 4110. Retrieved 2017/08/07.
• 2、 Gangula, Srinivas,Kolla, Naveen Kumar,Elati, Chandrasekar,Dongamanti, Ashok,Bandichhor, Rakeshwar. "Improved process for paroxetine hydrochloride substantially free from potential impurities". . p. 3344 - 3360. Retrieved 2012/10/08.