Paroxetine supplier | CasNO.61869-08-7

Name
Paroxetine
EINECS 682-717-4
CAS No. 61869-08-7
Article Data32
CAS DataBase
Density 1.213 g/cm³
Solubility
Melting Point 114-116 °C
Formula C₁₉H₂₀FNO₃
Boiling Point 451.674 °C at 760 mmHg
Molecular Weight 329.371
Flash Point 226.964 °C
Transport Information UN 3249
Appearance White solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Piperidine,3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, (3S-trans)-;(-)-Paroxetine;(-)-trans-4R-(4'-Fluorophenyl)-3S-((3',4'-methylenedioxyphenoxy)methyl)piperidine;Aropax;BRL 29060;Besitram;Casbol;FG 7051;Frosinor;Motivan;PaxPar;Paxetil;Paxil;
PSA 39.72000
LogP 3.65530

Synthetic route

: C25H25FN2O3

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With acetic acid; zinc at 20℃; for 6h;	98%
With acetic acid; zinc at 20℃; for 6h;	96%

: 105813-14-7
(3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; acetic acid; isopropyl alcohol at 50℃; under 4500.45 Torr; for 15h; stereoselective reaction;	97%
With hydrogen; palladium on activated charcoal In acetic acid; isopropyl alcohol at 50℃; under 4500.36 Torr; for 15h;	96%
With palladium on activated charcoal; hydrogen; acetic acid In isopropyl alcohol	92%
Stage #1: (3S,4R)-1-benzyl-4-(4-fluorophenyl)-3-[3,4-(methylenedioxy)-phenoxymethyl]piperidine With 1-chloroethyl chloroformate In 1,2-dichloro-ethane for 3h; Heating; Stage #2: In methanol for 2h; Heating;	54%

: 600135-90-8
(3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Stage #1: (3S,4R)-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)-1-vinyloxycarbonylpiperidine With hydrogenchloride In 1,2-dichloro-ethane for 0.75h; Stage #2: In ethanol for 1.5h; Heating;	96%

: 754183-64-7
(S)-5-(benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidin-2-one

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃;	90%

: 200572-35-6
(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.333333h;	75%
With trifluoroacetic acid In dichloromethane at 20℃; for 0.25h; Boc-deprotection;	72%
With trifluoroacetic acid In dichloromethane for 0.25h;	99 mg

: 1561215-70-0
(3R,4S)-5-amino-4-((benzo[d][1,3]dioxol-5-yloxy)methyl)-3-(4-fluorophenyl)pentan-1-ol

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 2.5h; Inert atmosphere;	71%

: (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(phenylsulfonyl)piperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With pyrrolidine; samarium diiodide In tetrahydrofuran; water at 20℃; for 0.0833333h;	61%

: 200114-10-9
(3S,4R)-3-(Benzo[1,3]dioxol-5-yloxymethyl)-4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid methyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water at 110℃; for 42h;	61%

: 200572-35-6
(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine

A: 61869-08-7, 72473-26-8, 105813-05-6, 105813-07-8, 112058-85-2, 130855-15-1
paroxetine

B: 61869-08-7
paroxetine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 1.5h; Title compound not separated from byproducts.;

: 216690-18-5
(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylic acid methyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: LiAlH4 / tetrahydrofuran / 20 h / Heating 2.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C 3.1: NaH / dimethylformamide / 0.33 h / 20 °C 3.2: 52 percent / dimethylformamide / 14 h / 90 °C 4.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme

: 533-31-3
Sesamol

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 0.33 h / 20 °C 1.2: 52 percent / dimethylformamide / 14 h / 90 °C 2.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme
Multi-step reaction with 3 steps 1.1: 80 percent / NaH / dimethylformamide / 4 h / Heating 2.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 3.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 3.2: 96 percent / ethanol / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 76 mg / NaOMe / methanol / 1.5 h / Heating 2: 72 percent / TFA / CH2Cl2 / 0.25 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 10 h / 85 °C / Inert atmosphere 2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: hydrazine hydrate / ethanol / 0.58 h / 20 - 85 °C / Inert atmosphere 4.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

: 201855-60-9
(3S,4R)-[1-benzyl-4-piperidin-3-yl-4-(4-fluorophenyl)]methanol

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: NaH / dimethylformamide / 0.33 h / 20 °C 2.2: 52 percent / dimethylformamide / 14 h / 90 °C 3.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme
Multi-step reaction with 3 steps 1.1: pyridine / 1 h / 10 °C 2.1: 81 mg / NaOMe / methanol / Heating 3.1: 1-chloroethyl formate / 1,2-dichloro-ethane / 3 h / Heating 3.2: 54 percent / methanol / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: triethylamine / toluene 2: sodium hydride / N,N-dimethyl-formamide 3: palladium on activated charcoal; hydrogen; acetic acid / isopropyl alcohol View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 20 °C / Inert atmosphere 2.2: 15 h / 90 °C / Inert atmosphere 3.1: acetic acid; palladium 10% on activated carbon; isopropyl alcohol; hydrogen / 15 h / 50 °C / 4500.45 Torr View Scheme

: 201855-71-2
Methanesulfonic acid (3S,4R)-1-benzyl-4-(4-fluoro-phenyl)-piperidin-3-ylmethyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 0.33 h / 20 °C 1.2: 52 percent / dimethylformamide / 14 h / 90 °C 2.1: 96 percent / hydrogen / Pd/C / acetic acid; propan-2-ol / 15 h / 50 °C / 4500.36 Torr View Scheme
Multi-step reaction with 2 steps 1.1: 81 mg / NaOMe / methanol / Heating 2.1: 1-chloroethyl formate / 1,2-dichloro-ethane / 3 h / Heating 2.2: 54 percent / methanol / 2 h / Heating View Scheme

: 511283-91-3
1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: chiral bis-lithium amide base / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 71 percent / tetrahydrofuran; hexane / -40 °C 2.1: LiAlH4 / tetrahydrofuran / Heating 3.1: pyridine / 1 h / 10 °C 4.1: 81 mg / NaOMe / methanol / Heating 5.1: 1-chloroethyl formate / 1,2-dichloro-ethane / 3 h / Heating 5.2: 54 percent / methanol / 2 h / Heating View Scheme

: 511284-07-4
(3S,4R)-1-benzyl-4-(4-fluorophenyl)-2,6-dioxopiperidine-3-carboxylic acid methyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: LiAlH4 / tetrahydrofuran / Heating 2.1: pyridine / 1 h / 10 °C 3.1: 81 mg / NaOMe / methanol / Heating 4.1: 1-chloroethyl formate / 1,2-dichloro-ethane / 3 h / Heating 4.2: 54 percent / methanol / 2 h / Heating View Scheme

: 347-93-3
3-chloro-4'-fluoropropiophenone

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating 2: Na2CO3 / CH2Cl2 / 0.5 h 3: 8.36 g / EtONa / ethanol / 0.5 h / Heating 4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 5: 79 percent / MeOH; NaH / toluene / 4 h / Heating 6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 7: CAN / acetonitrile; H2O / 0.5 h / 20 °C 8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 9: Cs2CO3 / o-xylene / 20 h / 130 °C 10: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

Yield

Multi-step reaction with 10 steps
1: 77 percent / Et3N / tetrahydrofuran / 4 h / Heating
2: Na2CO3 / CH2Cl2 / 0.5 h
3: 8.36 g / EtONa / ethanol / 0.5 h / Heating
4: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
5: 79 percent / MeOH; NaH / toluene / 4 h / Heating
6: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
7: CAN / acetonitrile; H2O / 0.5 h / 20 °C
8: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
9: Cs2CO3 / o-xylene / 20 h / 130 °C
10: 99 mg / TFA / CH2Cl2 / 0.25 h
View Scheme

: 37155-08-1
1-(4-fluorophenyl)-3-(4-methoxyphenylamino)propan-1-one

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: Na2CO3 / CH2Cl2 / 0.5 h 2: 8.36 g / EtONa / ethanol / 0.5 h / Heating 3: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 4: 79 percent / MeOH; NaH / toluene / 4 h / Heating 5: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 6: CAN / acetonitrile; H2O / 0.5 h / 20 °C 7: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 8: Cs2CO3 / o-xylene / 20 h / 130 °C 9: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

Yield

Multi-step reaction with 9 steps
1: Na2CO3 / CH2Cl2 / 0.5 h
2: 8.36 g / EtONa / ethanol / 0.5 h / Heating
3: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
4: 79 percent / MeOH; NaH / toluene / 4 h / Heating
5: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
6: CAN / acetonitrile; H2O / 0.5 h / 20 °C
7: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
8: Cs2CO3 / o-xylene / 20 h / 130 °C
9: 99 mg / TFA / CH2Cl2 / 0.25 h
View Scheme

: 200572-33-4
(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Cs2CO3 / o-xylene / 20 h / 130 °C 2: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0.17 h / 20 °C 2: 0.127 g / NaH / dimethylformamide / 0.25 h / Heating 3: TFA / CH2Cl2 / 1.5 h View Scheme
Multi-step reaction with 3 steps 1: 100 mg / pyridine / 1 h / 10 °C 2: 76 mg / NaOMe / methanol / 1.5 h / Heating 3: 72 percent / TFA / CH2Cl2 / 0.25 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 1.5 h / 20 °C 2: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 20 °C / Reflux 3: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C View Scheme

: 125224-43-3
(3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 2: Cs2CO3 / o-xylene / 20 h / 130 °C 3: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

: 607375-32-6
4-(4-fluorophenyl)-1-(4-methoxyphenyl)-5,6-dihydro-1H-pyridin-2-one

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 2: 79 percent / MeOH; NaH / toluene / 4 h / Heating 3: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 4: CAN / acetonitrile; H2O / 0.5 h / 20 °C 5: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 6: Cs2CO3 / o-xylene / 20 h / 130 °C 7: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
2: 79 percent / MeOH; NaH / toluene / 4 h / Heating
3: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
4: CAN / acetonitrile; H2O / 0.5 h / 20 °C
5: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
6: Cs2CO3 / o-xylene / 20 h / 130 °C
7: 99 mg / TFA / CH2Cl2 / 0.25 h
View Scheme

: 607375-33-7
(4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-2-one

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 79 percent / MeOH; NaH / toluene / 4 h / Heating 2: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 3: CAN / acetonitrile; H2O / 0.5 h / 20 °C 4: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 5: Cs2CO3 / o-xylene / 20 h / 130 °C 6: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

: 607375-35-9
[(3S,4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-piperidin-3-yl]methanol

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: CAN / acetonitrile; H2O / 0.5 h / 20 °C 2: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 3: Cs2CO3 / o-xylene / 20 h / 130 °C 4: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

: 607375-34-8
(3S,4R)-4-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-oxopiperidin-3-carboxylic acid methyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 2: CAN / acetonitrile; H2O / 0.5 h / 20 °C 3: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 4: Cs2CO3 / o-xylene / 20 h / 130 °C 5: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

: 1027570-33-7
N-[3-(4-fluoro-phenyl)-3-oxo-propyl]-N-(4-methoxy-phenyl)-malonamic acid ethyl ester

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 8.36 g / EtONa / ethanol / 0.5 h / Heating 2: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h 3: 79 percent / MeOH; NaH / toluene / 4 h / Heating 4: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating 5: CAN / acetonitrile; H2O / 0.5 h / 20 °C 6: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C 7: Cs2CO3 / o-xylene / 20 h / 130 °C 8: 99 mg / TFA / CH2Cl2 / 0.25 h View Scheme

Yield

Multi-step reaction with 8 steps
1: 8.36 g / EtONa / ethanol / 0.5 h / Heating
2: 89 percent / CuCl2; t-BuONa; (R)-p-tolBINAP / PMHS; tert-amyl alcohol / fluorobenzene / 0.75 h
3: 79 percent / MeOH; NaH / toluene / 4 h / Heating
4: 98 percent / BH3 / tetrahydrofuran / 18 h / Heating
5: CAN / acetonitrile; H2O / 0.5 h / 20 °C
6: 268 mg / NaOH / toluene; H2O / 3 h / 20 °C
7: Cs2CO3 / o-xylene / 20 h / 130 °C
8: 99 mg / TFA / CH2Cl2 / 0.25 h
View Scheme

: 105812-81-5
(3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 89 percent / trimethylamine hydrochloride / CH2Cl2 / 4 h / cooling 2.1: 80 percent / NaH / dimethylformamide / 4 h / Heating 3.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 4.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 4.2: 96 percent / ethanol / 1.5 h / Heating View Scheme

: 110429-36-2
(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 2.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 2.2: 96 percent / ethanol / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: toluene / 3.75 h / 100 - 105 °C / Large scale reaction 1.2: 1 h / 60 °C 1.3: 25 - 35 °C 2.1: water; sodium hydroxide / isopropyl alcohol / 82 - 85 °C / Large scale reaction View Scheme

: 317323-77-6
(3S,4R)-trans-4-(4-fluorophenyl)-1-methyl-3-p-toluenesulphonyloxymethyl-piperidine

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 80 percent / NaH / dimethylformamide / 4 h / Heating 2.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 3.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 3.2: 96 percent / ethanol / 1.5 h / Heating View Scheme

: 200572-34-5
(3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.127 g / NaH / dimethylformamide / 0.25 h / Heating 2: TFA / CH2Cl2 / 1.5 h View Scheme
Multi-step reaction with 2 steps 1: 76 mg / NaOMe / methanol / 1.5 h / Heating 2: 72 percent / TFA / CH2Cl2 / 0.25 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran; mineral oil / 6 h / 20 °C / Reflux 2: trifluoroacetic acid / dichloromethane / 0.33 h / 20 °C View Scheme

: (3R,4S)-3-(4-Fluoro-phenyl)-4-nitromethyl-5-triisopropylsilanyloxy-pentanal

: 61869-08-7
paroxetine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 0.761 g / NaBH4 / methanol / 1 h 2: ammonium formate / Pd/C / methanol / 0.5 h / Heating 3: 0.702 g / CH2Cl2 / 2 h / 20 °C 4: Et3N / tetrahydrofuran / 0.17 h / 20 °C 5: KOt-Bu / tetrahydrofuran / 0.5 h / 0 °C 6: 0.327 g / TBAF / tetrahydrofuran / 12 h 7: Et3N / CH2Cl2 / 0.17 h / 20 °C 8: 0.127 g / NaH / dimethylformamide / 0.25 h / Heating 9: TFA / CH2Cl2 / 1.5 h View Scheme

Yield

Multi-step reaction with 9 steps
1: 0.761 g / NaBH4 / methanol / 1 h
2: ammonium formate / Pd/C / methanol / 0.5 h / Heating
3: 0.702 g / CH2Cl2 / 2 h / 20 °C
4: Et3N / tetrahydrofuran / 0.17 h / 20 °C
5: KOt-Bu / tetrahydrofuran / 0.5 h / 0 °C
6: 0.327 g / TBAF / tetrahydrofuran / 12 h
7: Et3N / CH2Cl2 / 0.17 h / 20 °C
8: 0.127 g / NaH / dimethylformamide / 0.25 h / Heating
9: TFA / CH2Cl2 / 1.5 h
View Scheme

: 108-24-7
acetic anhydride

: 61869-08-7
paroxetine

: N-acetylparoxetine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 16h;	98%

: 76-05-1
trifluoroacetic acid

: 61869-08-7
paroxetine

: (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(2,2,2-trifluoroethyl)piperidine

Conditions

Conditions	Yield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 8h; Glovebox; Molecular sieve; Schlenk technique;	96%

: 98-60-2
4-chlorobenzenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(4-chlorobenzenesulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	90%

: 106-94-5
propyl bromide

: 61869-08-7
paroxetine

: C22H26FNO3

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	88%

: 50-00-0
formaldehyd

: 61869-08-7
paroxetine

: 110429-36-2
(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine

Conditions

Conditions	Yield
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 14h;	87%

: 61869-08-7
paroxetine

: 1939-99-7
benzenesulfonyl chloride

: N-(benzylsulphonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 85-46-1
1-Naphthalenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(naphthalene-1-ylsulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 93-11-8
2-Naphthalenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(naphthalene-2-ylsulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 98-09-9
benzenesulfonyl chloride

: 61869-08-7
paroxetine

: (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-(phenylsulfonyl)piperidine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 98-59-9
p-toluenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(4-toluenesulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 773-64-8
2-mesitylenesulphonyl chloride

: 61869-08-7
paroxetine

: N-(2-mesitylenesulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 1788-10-9
4-Acetylbenzenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(4-acetylbenzenesulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	85%

: 124-38-9
carbon dioxide

: 61869-08-7
paroxetine

: 533935-67-0
N-formyl paroxetine ((3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carbaldehyde)

Conditions

Conditions	Yield
With cyclopentadienyl iron(II) dicarbonyl dimer; tributylphosphine; phenylsilane In acetonitrile at 30℃; under 760.051 Torr; for 36h; Schlenk technique; Sealed tube;	85%

: 61869-08-7
paroxetine

: C19H14(2)H6FNO3

Conditions

Conditions	Yield
With [(N,N’-bis(1R,2R,3R,5S)-(−)-isopinocampheyl-1,2-ethanediimine-radical)NiI(μ2-H)]2; deuterium at -196 - 80℃; under 760.051 Torr; for 24h; Reagent/catalyst; Sealed tube;	81%

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 61869-08-7
paroxetine

: N-(4-acetamidobenzenesulfonyl)paroxetine

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; for 3h; pH=9 - 10; Green chemistry;	75%

: 930-88-1
N-methylmaleimide

: 42254-80-8
S-methyl thiosulfate O-sodium salt

: 61869-08-7
paroxetine

: 3-((3R,4S)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidin-1-yl)-1-methyl-4-(methylthio)-1H-pyrrole-2,5-dione

Conditions

Conditions	Yield
With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; for 24h; Schlenk technique;	73%

...Expand

Paroxetine Specification

The Paroxetine, with the CAS registry number 61869-08-7, is also known as (-)-trans-4R-(4'-Fluorophenyl)-3S-((3',4'-methylenedioxyphenoxy)methyl)piperidine. It belongs to the product categories of Fluorobenzene; APIs; Paroxetine; Inhibitors; Intermediates & Fine Chemicals; Isotope Labeled Compounds; Pharmaceuticals. This chemical's molecular formula is C₁₉H₂₀FNO₃ and molecular weight is 329.37. What's more, its systematic name is (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine. Its classification codes are: (1)Antidepressant; (2)Antidepressive Agents; (3)Antidepressive agents, second-generation; (4)Central Nervous System Agents; (5)Human Data; (6)Neurotransmitter Agents; (7)Neurotransmitter Uptake Inhibitors; (8)Psychotropic Drugs; (9)Reproductive Effect; (10)Serotonin Agents; (11)Serotonin uptake inhibitors. This chemical is an antidepressant drug of the SSRI type. Paroxetine is used to treat major depression, obsessive-compulsive disorder, panic disorder, social anxiety, posttraumatic stress disorder, and generalized anxiety disorder in adult outpatients.

Physical properties of Paroxetine are: (1)ACD/LogP: 3.701; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.64; (4)ACD/LogD (pH 7.4): 1.48; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 2.29; (7)ACD/KOC (pH 5.5): 2.11; (8)ACD/KOC (pH 7.4): 14.73; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 39.72 Å²; (13)Index of Refraction: 1.561; (14)Molar Refractivity: 87.949 cm³; (15)Molar Volume: 271.517 cm³; (16)Polarizability: 34.866×10^-24cm³; (17)Surface Tension: 45.5 dyne/cm; (18)Density: 1.213 g/cm³; (19)Flash Point: 226.964 °C; (20)Enthalpy of Vaporization: 71.076 kJ/mol; (21)Boiling Point: 451.674 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1[C@@H]2CCNC[C@H]2COc3ccc4c(c3)OCO4)F
(2)Std. InChI: InChI=1S/C19H20FNO3/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18/h1-6,9,14,17,21H,7-8,10-12H2/t14-,17-/m0/s1
(3)Std. InChIKey: AHOUBRCZNHFOSL-YOEHRIQHSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	oral	6700ug/kg (6.7mg/kg)	BEHAVIORAL: EXCITEMENT	American Journal of Emergency Medicine. Vol. 11, Pg. 682, 1993.
women	TDLo	oral	400ug/kg (.4mg/kg)	PERIPHERAL NERVE AND SENSATION: PARESTHESIS	Journal of Clinical Psychiatry. Vol. 58, Pg. 175, 1997.
women	TDLo	oral	400ug/kg (.4mg/kg)	BEHAVIORAL: REGIDITY PERIPHERAL NERVE AND SENSATION: FASCICULATIONS	British Journal of Psychiatry. Vol. 169, Pg. 522, 1996.
women	TDLo	oral	1400ug/kg/7W- (1.4mg/kg)		American Journal of Psychiatry. Vol. 153, Pg. 134, 1996.
women	TDLo	oral	2800ug/kg/7D- (2.8mg/kg)		Medical Journal of Australia. Vol. 163, Pg. 390, 1995.
women	TDLo	oral	2800ug/kg/7D- (2.8mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION	Medical Journal of Australia. Vol. 163, Pg. 390, 1995.
women	TDLo	oral	4200ug/kg/3W- (4.2mg/kg)	ENDOCRINE: HYPERGLYCEMIA	Annals of Internal Medicine. Vol. 125, Pg. 782, 1996.
women	TDLo	oral	5600ug/kg/2W- (5.6mg/kg)	BEHAVIORAL: IRRITABILITY BEHAVIORAL: WAKEFULNESS BEHAVIORAL: TOXIC PSYCHOSIS	Journal of the American Academy of Child and Adolescent Psychiatry. Vol. 36, Pg. 445, 1997.
women	TDLo	oral	8400ug/kg/21D (8.4mg/kg)		Netherlands Journal of Medicine. Vol. 51, Pg. 237, 1997.
women	TDLo	oral	8400ug/kg/21D (8.4mg/kg)	LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA BEHAVIORAL: COMA	Netherlands Journal of Medicine. Vol. 51, Pg. 237, 1997.
women	TDLo	oral	11200ug/kg/8W (11.2mg/kg)	PERIPHERAL NERVE AND SENSATION: FASCICULATIONS	Journal of Clinical Pyschopharmacology. Vol. 16, Pg. 258, 1996.

Product Name

Paroxetine

Synthetic route

Paroxetine Specification

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