132335-44-5

Basic information

• Product Name: (S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine
• Synonyms: (S)-(-)-N-DIMETHYL-3-HYDROXY-3-(2-THIENYL)-PROPANAMINE;S-(-)-N,N-DIMETHYL-3-HYDROXY-3-(2-THIENYL)PROPANAMINE;(S)-1-HYDROXY-1-(2-THIENYL)-3-DIMETHYLAMINOPROPANE;(S)-1-BETA-HYDROXY-1-(2-THIENYL)-3-DIMETHYLAMINOPROPANE;(s)-3-(dimethylamino)-1-(2-thienyl)-1-propanol;(S)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)-2-propanamine;Duloxetine intermediate AA;(S)-(-)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propylamine
• CAS NO: 132335-44-5
• Molecular Formula: C₉H₁₅NOS
• Molecular Weight: 185.29
• EINECS: 1312995-182-4
• Product Categories: Chemical intermediate for Duloxetine Hydrochloride;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 132335-44-5.mol
• Article Data: 46

Chemical Properties

• Melting Point: 78-80°C
• Boiling Point: 290°C
• Flash Point: 129°C
• Appearance: /
• Density: 1.111
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.74±0.20(Predicted)
• CAS DataBase Reference: (S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine(132335-44-5)
• EPA Substance Registry System: (S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine(132335-44-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 132335-44-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C9H15NOS/c1-10(2)6-5-8(11)9-4-3-7-12-9/h3-4,7-8,11H,5-6H2,1-2H3/t8-/m0/s1

Synthetic route

(S)-N,N-dimethyl-N-[3-hydroxy-3-(2-thienyl)propyl]-ammonium (S)-mandelate (287737-72-8) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With sodium hydroxide In water for 0.5h; pH=11 - 12;	95%
With ammonium hydroxide In tert-butyl methyl ether	92.1%
With sodium hydroxide In tert-butyl methyl ether; water at 20℃; for 0.5h; pH=9;

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With glucose dehydrogenase; D-glucose; Rhodosporidium toruloides carbonyl reductase 9 from Escherichia coli; NADPH; sodium hydroxide In aq. phosphate buffer at 30℃; for 4h; pH=7; Kinetics; Temperature; Enzymatic reaction; enantioselective reaction;	92.1%
With hydrogen; sodium hydrogencarbonate; (2R,4R)-4-(dicyclohexylphosphino)-2-(diphenylphosphino-methyl)-N-methyl-aminocarbonyl-pyrrolidine; di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium In methanol; water at 30℃; under 75007.5 Torr; for 20h;
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; sodium hydroxide / water / 7 h / 20 - 71 °C 2: toluene / 0.5 h / 80 °C 3: sodium hydroxide / water View Scheme

3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol (13636-02-7, 132335-44-5, 132335-49-0) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
Stage #1: 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol With tert-butyl methyl ether; (S)-Mandelic acid Stage #2: With sodium hydroxide	92%
With (S)-Mandelic acid In methanol; toluene at 20 - 95℃; for 1.5h; pH=1 - 12;	34%
Multi-step reaction with 2 steps 1: toluene / 0.5 h / 80 °C 2: sodium hydroxide / water View Scheme

tri(3-dimethylamino-1-(thiophen-2-yl)propyl)borate → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With methanol at 80℃; for 20h; Concentration;	92%

dimethyl amine (124-40-3) + (S)-3-chloro-1-(thiophen-2-yl)propan-1-ol (164071-56-1) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With potassium iodide In methanol; water at 80℃; for 8h;	89%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one (13196-35-5) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With potassium tert-butylate; hydrogen; RuCl2[(R)-(DM-BINAP)][(R)-DAIPEN] In isopropyl alcohol; tert-butyl alcohol at 28℃; for 6h;	80%
With hydrogen; (2R,2'R)-bis(diphenylphosphino)-(1R,1'R)-dicyclopentane; 1,1-dimethylethylenediamine; [RuCl2(dmf)n]; sodium t-butanolate In ethanol; dichloromethane at 20℃; under 5320 Torr; for 15h;
With RuCl2(1,1'-bis(diphenyphosphino)ferrocene)[(1S,1'S)-6,6'-dibromo-1,1'-biisoindoline]; potassium tert-butylate; hydrogen In propan-1-ol at 20℃; under 38002.6 Torr; for 30h; Inert atmosphere; Autoclave; optical yield given as %ee; enantioselective reaction;

C11H17NO2S → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphoric acid / water / 18 h / 40 - 45 °C 2: ethanol; tert-butyl methyl ether / 50 °C 3: ammonium hydroxide / tert-butyl methyl ether View Scheme

(S)-N,N-dimethyl-3-(p-nitrobenzoate)-3-(thiophen-2-yl)propylamine → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
In methanol at 20℃; for 2h; Alkaline conditions;	26.4 g

(S)-N,N-dimethyl-3-hydroxy-3-(thiophen-2-yl)propylamine mandelate → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With water; sodium hydroxide	30.2 g

3-dimethylamino-1-thiophen-2-ylpropenone (34772-98-0) → (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 8 h / Reflux 2: ethanol; tert-butyl methyl ether / 1 h / Reflux 3: sodium hydroxide / water / 0.5 h / pH 11 - 12 View Scheme

C29H26BNO3S → α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol (132335-49-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5)

Conditions	Yield
With hydrogenchloride In ethyl acetate at 20℃; for 1h;	A n/a B 65 mg

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → N-methyl-(S)-duloxetine (132335-46-7)

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide at 60℃; for 1.16667h; Stage #2: 1-Fluoronaphthalene In dimethyl sulfoxide at 60℃; for 24h; Solvent; Reagent/catalyst;	93.9%
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Stage #2: With Potassium benzoate In dimethyl sulfoxide; mineral oil for 0.5h; Stage #3: 1-Fluoronaphthalene In dimethyl sulfoxide; mineral oil at 65℃; for 8h;	92%
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.5h; Stage #2: 1-Fluoronaphthalene In dimethyl sulfoxide; mineral oil at 40 - 50℃; for 8h;	90%

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) + acetyl chloride (75-36-5) → (S)-N-[3-acetoxy-3-(thien-2-yl)propyl]-N,N-dimethylamine

Conditions	Yield
With triethylamine In chloroform at 5 - 20℃; for 2.16667h;	92%
With triethylamine In toluene at 25℃; for 6.5h;	60 g

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-N,N-dimethyl-3-(1-napthaleneoxy)-2-thiophenepropanamine oxalate

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With potassium hydroxide; 18-crown-6 ether In dimethyl sulfoxide at 60℃; for 1h; Stage #2: 1-Fluoronaphthalene In dimethyl sulfoxide for 2h; Stage #3: With oxalic acid In ethyl acetate for 1h;	88%

4-fluorobenzo[1,3]dioxolane (943830-74-8) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-N,N-dimethyl-3-[(benzo[1,3]dioxolan-4-yl)-oxy]-3-(thiophen-2-yl)-propylamine

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide; mineral oil at 60℃; for 0.5h; Stage #2: With Potassium benzoate In dimethyl sulfoxide; mineral oil for 0.333333h; Stage #3: 4-fluorobenzo[1,3]dioxolane In dimethyl sulfoxide; mineral oil at 60℃; for 8h;	82%
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With Potassium benzoate; sodium hydride In dimethyl sulfoxide at 60℃; for 0.5h; Stage #2: 4-fluorobenzo[1,3]dioxolane In dimethyl sulfoxide at 60℃; for 8h;	4.8 g

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) + isobutyl chloroformate (543-27-1) → (S)-3-methylamino-1-(2-thienyl)-1-propanol (116539-55-0)

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol; isobutyl chloroformate With triethylamine In toluene at 20 - 30℃; for 6h; Stage #2: With potassium hydroxide In methanol at 75℃; for 3.5h; Heating / reflux;	79.6%

4-bromo-2-chloro-1-((3-fluorobenzyl)oxy)benzene + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → C22H23ClFNO2S

Conditions	Yield
With copper(l) iodide; N1, N2-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating;	70%

1-Bromonaphthalene (90-11-9) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → N-methyl-(S)-duloxetine (132335-46-7)

Conditions	Yield
With copper(l) iodide; N1, N2-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating;	65%

1-Fluoronaphthalene (321-38-0) + oxalic acid (144-62-7) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine oxalate (132335-47-8)

Conditions	Yield
Stage #1: 1-Fluoronaphthalene; (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With tetrabutylammomium bromide; sodium hydroxide In dimethyl sulfoxide at 50 - 65℃; Stage #2: oxalic acid In toluene at 55 - 60℃; for 1h; optical yield given as %ee; enantioselective reaction;	59.9%
Stage #1: 1-Fluoronaphthalene; (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With potassium tert-butylate at 90 - 100℃; Stage #2: oxalic acid In methanol at 0 - 30℃;

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → duloxetine hydrochloride (136434-34-9)

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-Fluoronaphthalene In dimethyl sulfoxide at 60℃; Inert atmosphere;	56%
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / 20 °C 1.2: 8 h / 40 - 50 °C 2.1: carbonochloridic acid 1-chloro-ethyl ester / dichloromethane / 3 h / 0 - 5 °C / Reflux 2.2: 1 h / 50 °C View Scheme

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine oxalate (132335-47-8)

Conditions	Yield
With sodium hydride 1) DMSO, 25 deg C, 25 min 2) 48-72 h, 45-50 deg C; Yield given. Multistep reaction;

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → Duloxetine (116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) NaH / 1) DMSO, 25 deg C, 25 min 2) 48-72 h, 45-50 deg C 2: 1) ClCO2CH2CCl3, Et3N, HCl 2) Zn-dust, 2.5percent formic acid / 1) toluene, 30 min, 25 deg C 2) DMF View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.25 h / 25 °C 1.2: 0.25 h / 25 - 30 °C 1.3: 48 h / 25 - 30 °C 2.1: N-ethyl-N,N-diisopropylamine / toluene / 0.17 h 2.2: Reflux 3.1: potassium hydroxide / polyethylene glycol-400 / 16 h / 65 - 70 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.5 h / 20 °C 1.2: 0.5 h 1.3: 8 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine / toluene / 0.17 h / 45 °C 2.2: 2 h / 55 °C 3.1: sodium hydroxide / water; dimethyl sulfoxide / 8 h / 45 - 55 °C / Alkaline conditions View Scheme
Multi-step reaction with 2 steps 1: sodium hydride 2: potassium hydroxide / ethanol; toluene / 2 h / 85 - 100 °C View Scheme

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) + phenyl chloroformate (1885-14-9) → (S)-3-methylamino-1-(2-thienyl)-1-propanol (116539-55-0)

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol; phenyl chloroformate With triethylamine In tert-butyl methyl ether at -5 - 20℃; for 4h; Stage #2: With potassium hydroxide In methanol; tert-butyl methyl ether for 2h; Heating / reflux;

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) + phenyl chloroformate (1885-14-9) → phenyl (RS)-N-methyl-N-[3-phenyloxycarbonyloxy-3-(thien-2-yl)propyl]carbamate (625853-19-2)

Conditions	Yield
With triethylamine In acetonitrile at 5 - 20℃; for 2h;

1-Fluoronaphthalene (321-38-0) + Potassium benzoate (582-25-2) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, phosphoric acid salt (161005-84-1)

Conditions	Yield
With phosphoric acid In hexane; water; dimethyl sulfoxide; mineral oil

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → Duloxetine (116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1)

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane at 60℃; for 8h; Product distribution / selectivity;
With potassium hydroxide In Tetraethylene glycol dimethyl ether at 60℃; for 8h; Product distribution / selectivity;
With potassium hydroxide In diethylene glycol dimethyl ether at 60℃; for 8h; Product distribution / selectivity;
With potassium hydroxide In Triethylene glycol dimethyl ether at 60℃; for 8h; Product distribution / selectivity;

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (R)-Duloxetine (116539-60-7) + Duloxetine (116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 60℃; for 8h; Product distribution / selectivity;

1-Fluoronaphthalene (321-38-0) + (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol (132335-44-5) → (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, phosphoric acid salt (161005-84-1)

Conditions	Yield
Stage #1: 1-Fluoronaphthalene; (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With potassium hydroxide In diethylene glycol dimethyl ether at 120℃; for 3 - 6h; Stage #2: With phosphoric acid In water; ethyl acetate for 1.08333 - 1.25h;
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol With sodium hydride In dimethyl sulfoxide at 20℃; for 2h; Stage #2: 1-Fluoronaphthalene With potassium p-methyl benzoate In dimethyl sulfoxide at 20 - 65℃; for 5h; Stage #3: With phosphoric acid In ethyl acetate for 0.5h; pH=2;

Upstream product

• 34772-98-0 3-dimethylamino-1-thiophen-2-ylpropenone 
• 40570-64-7 3-chloro-1-(2-thienyl)propan-1-one 
• 124-40-3 dimethyl amine 
• 164071-56-1 (S)-3-chloro-1-(thiophen-2-yl)propan-1-ol 
• 13636-02-7 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 
• 959392-20-2 (S) 3-(dimethylamino)-1-(thiophen-2-yl) propan-1-ol mandelate 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 88-15-3 2-Acetylthiophene 
• 287737-72-8 (S)-N,N-dimethyl-N-[3-hydroxy-3-(2-thienyl)propyl]-ammonium (S)-mandelate 
• 13196-35-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 74-88-4 methyl iodide 

Downstream Products

• 132335-47-8 (S)-N,N-dimethyl-3-(1-naphthyloxy)-3-(2-thienyl)propanamine oxalate 
• 116817-11-9 N,N-dimethylamino-3-(1-naphthanyloxy)-3-(2-thienyl)-1-propanamine 
• 287737-72-8 (S)-N,N-dimethyl-N-[3-hydroxy-3-(2-thienyl)propyl]-ammonium (S)-mandelate 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 
• 116817-12-0 N,N-dimethyl-3-(1-naphthalenyloxy)-3-(thien-2-yl)propanamine oxalate 
• 136434-34-9 duloxetine hydrochloride 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 947686-09-1 (S)-N-methyl-N-phenoxycarbonyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propylamine 
• 1369583-87-8 N-[4-(2-methoxyphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-88-9 N-[4-(3-trifluoromethylphenylpiperazinyl)propionyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-90-3 N-[4-(4-(2-methoxyphenylpiperazinyl)butyryl)]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-91-4 N-[4-(4-(3-trifluoromethylphenylpiperazinyl)butyryl)]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-93-6 N-[4-(2-methoxyphenylpiperazinyl)propyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 
• 1369583-94-7 N-[4-(3-trifluoromethylphenylpiperazinyl)propyl]-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine 

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