(3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrate;hydrochloride

Base Information

• Chemical Name: (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrate;hydrochloride
• CAS No.: 110429-35-1
• Molecular Formula: C19H20FNO3 . ClH . 1/2H2O
• Molecular Weight: 365.832
• Hs Code.: 29349990
• European Community (EC) Number: 600-962-7
• NCI Thesaurus Code: C82238
• ChEMBL ID: CHEMBL1256912
• Mol file: 110429-35-1.mol

Synonyms:Aropax;BRL 29060;BRL-29060;BRL29060;FG 7051;FG-7051;FG7051;Paroxetine;Paroxetine Acetate;Paroxetine Hydrochloride;Paroxetine Hydrochloride Anhydrous;Paroxetine Hydrochloride Hemihydrate;Paroxetine Hydrochloride, Hemihydrate;Paroxetine Maleate;Paroxetine, cis-(+)-Isomer;Paroxetine, cis-(-)-Isomer;Paroxetine, trans-(+)-Isomer;Paxil;Seroxat

Chemical Property of (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrate;hydrochloride

Chemical Property:

• Melting Point: 121-131oC
• Boiling Point: 451.7oC at 760mmHg
• Flash Point: 227oC
• PSA: 39.72000
• Density: 1.213g/cm3
• LogP: 4.45730
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Slightly soluble in water, freely soluble in methanol, sparingly soluble in ethanol (96 per cent) and in methylene chloride.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 383.1299641
• Heavy Atom Count: 26
• Complexity: 402

Purity/Quality:

99.5% ^*data from raw suppliers

Paroxetine hydrochloride hemihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C,Xn
• Hazard Codes: F,C,Xn
• Statements: 11-34-36/37/38-22
• Safety Statements: 16-26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCC(C1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4.O.Cl
• Isomeric SMILES: C1CNC[C@H]([C@@H]1C2=CC=C(C=C2)F)COC3=CC4=C(C=C3)OCO4.O.Cl
• Recent EU Clinical Trials: Initiation of agomelatine after antidepressant treatment by SSRI or SNRI in outpatients suffering Major Depressive Disorder.
• Uses: Paroxetine Hydrochloride, is a selective serotonin reuptake inhibitor (SSRI) antidepressant used to treat depression, panic attacks, obsessive-compulsive disorder (OCD), anxiety disorders, post-traumatic stress disorder, and a severe form of premenstrual syndrome (premenstrual dysphoric disorder). Antidepressant;5-HT uptake inhibitor Paroxetine hydrochloride hemihydrate has been used: as an antidepressant to study its effects on neural stem cells (NSCs) from embryonic rat hippocampus in vitro; as a CYP 2D6 inhibitor to study its effects on the in vitro?production by human recombinant CYP 2D6 of the phenolic metabolites; as an antidepressant to study its effects on the expression of pituitary adenylate cyclase activating polypeptide (PACAP), its receptors and brain-derived neurotrophic factor (BDNF) in rat primary hippocampal neurons

Technology Process of (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrate;hydrochloride

There total 58 articles about (3S,4R)-3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine;hydrate;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:

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

(3S,4R)-3-(Benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid methyl ester

4-(4-fluoro-phenyl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

4-(4-fluoro-phenyl)-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid methyl ester

Downstream raw materials:

desfluoro paroxetine

Desmethylene-Paroxetine

S-(2-hydroxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate

S-(2-bromoxyethyl) (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carbothioate

Refernces

• 1、 Krautwald, Simon,Schafroth, Michael A.,Sarlah, David,Carreira, Erick M.. "Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis". . p. 3020 - 3023. Retrieved 2014/03/21.
• 2、 -. "SULFATED GALACTANS WITH ANTITHROMBOTIC ACTIVITY, PHARMACEUTICAL COMPOSITION, METHOD FOR TREATING OR PROPHYLAXIS OF ARTERIAL OR VENOUS THROMBOSIS, METHOD OF EXTRACTION AND USE THEREOF". Page/Page column 6-7. . Retrieved 2009/12/23.