5424-47-5

Basic information

• Product Name: 2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL
• Synonyms: SALOR-INT L158135-1EA;2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL;3-(DIMETHYLAMINO)-1-(THIOPHEN-2-YL)PROPAN-1-ONE HYDROCHLORIDE;3-DIMETHYLAMINO-1-(2-THIENYL)-1-PROPANONE HCl;2-Thienyl-2-dimethylaminoethyl ketone hydrochloride;3-DiMethylaMino-1-(2-thienyl)-1-propanone hydrochloride, 97+%;2-[3-(Dimethylamino)propionyl]thiophene Hydrochloride;1-Propanone-3-(diMethylaMino)-1-(2-thienyl)- hydrochloride
• CAS NO: 5424-47-5
• Molecular Formula: C₉H₁₃NOS*ClH
• Molecular Weight: 219.73
• EINECS: 1806241-263-5
• Mol File: 5424-47-5.mol
• Article Data: 34

Chemical Properties

• Melting Point: 176.0 to 182.0 °C
• Boiling Point: 282.6 °C at 760 mmHg
• Flash Point: 124.7 °C
• Appearance: /
• Density: 1.096 g/cm³
• Vapor Pressure: 0.00332mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL(5424-47-5)
• EPA Substance Registry System: 2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL(5424-47-5)

Safety Data

• Hazardous Substances Data: 5424-47-5(Hazardous Substances Data)

Usage

Uses

3-(Dimethylamino)-1-(2-thienyl)-1-propanone, HCl

InChI:InChI=1/C9H13NOS.ClH/c1-10(2)6-5-8(11)9-4-3-7-12-9;/h3-4,7H,5-6H2,1-2H3;1H

Synthetic route

2-Acetylthiophene (88-15-3) + formaldehyd (50-00-0) + N,N-dimethylammonium chloride (506-59-2) → 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5)

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol for 6h; Reflux;	94%
With hydrogenchloride In water; isopropyl alcohol for 8h; Reflux;	92.4%
With hydrogenchloride In ethanol for 24h; Heating;	91%

2-Acetylthiophene (88-15-3) + N,N-dimethyl(methylene)ammonium chloride (30354-18-8) → 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5)

Conditions	Yield
In acetonitrile at 20℃;	61%

2-Acetylthiophene (88-15-3) + N,N-dimethylammonium chloride (506-59-2) → 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5)

Conditions	Yield
With hydrogenchloride In isopropyl alcohol
With hydrogenchloride; paraformaldehyde In ethanol	75.0 g (73%)
With hydrogenchloride; paraformaldehyde In ethanol	3.391 kg (85.7%)

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol (13636-02-7, 132335-44-5, 132335-49-0)

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In methanol; water at 35 - 40℃; for 2h;	95%
With sodium tetrahydroborate; sodium hydroxide In ethanol; water at 20℃; pH=11 -Ca. 12;	93.5%
With sodium tetrahydroborate; sodium hydroxide In water at 20 - 71℃; for 7h;	90.1%

1-indoline (496-15-1) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(indolin-1-yl)-1-(thiophen-2-yl)-1-propanone (1267977-01-4)

Conditions	Yield
In ethanol; water for 1h; Reflux;	95%

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-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + p-Chlorothiophenol (106-54-7) → 3-(4-chlorophenylthio)-1-(thiophen-2-yl)-1-propanone (320422-69-3)

Conditions	Yield
In ethanol; water for 1h; Reflux;	83%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + 2-Naphthalenethiol (91-60-1) → 3-(naphthalen-2-ylthio)-1-(thiophen-2-yl)-1-propanone (23117-91-1)

Conditions	Yield
In ethanol; water for 1h; Reflux;	83%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + 2-carbomethoxyaniline (134-20-3) → methyl 2-(3-oxo-3-(thiophen-2-yl)propylamino)benzoate (893770-14-4)

Conditions	Yield
In ethanol; water for 1h; Reflux;	82%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + 4-methylthiosemicarbazide (6610-29-3) → 1-(N-methylthiocarbamoyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole (1253196-01-8)

Conditions	Yield
Stage #1: 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride; 4-methylthiosemicarbazide In isopropyl alcohol Inert atmosphere; Stage #2: With potassium hydroxide In ethanol; isopropyl alcohol	78%

Lawessons reagent (19172-47-5) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 2-(4-methoxyphenyl)-6-(thiophen-2-yl)-4H-1,3,2-oxathiaphosphorine-2-sulfide (1467081-71-5)

Conditions	Yield
In toluene for 12h; Reflux;	78%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol (132335-49-0)

Conditions	Yield
With methanol; sodium tetrahydroborate; sodium hydroxide In water at 0℃; for 15h;	78%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / methanol; water / 4 h / 0 - 20 °C / Inert atmosphere 2: diethylamine / ethanol; n-heptane / Resolution of racemate View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; sodium hydroxide / water; ethanol / 20 °C / pH 11 -Ca. 12 2: ethanol; tert-butyl methyl ether / 0.75 h / Reflux View Scheme

1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide (26482-00-8) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 6-(thiophen-2-yl)-2,2'-bipyridine (123760-40-7)

Conditions	Yield
With ammonium acetate In acetic acid 100 deg C 10 min, 105 deg C 4 h;	75%
With ammonium acetate In acetic acid Krohnke pyridine synthesis; Reflux;	65%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + thiosemicarbazide (79-19-6) → 1-thiocarbamoyl-3-(thiophen-2-yl)-4,5-dihydropyrazole (1253195-94-6)

Conditions	Yield
Stage #1: 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride; thiosemicarbazide In isopropyl alcohol Inert atmosphere; Stage #2: With potassium hydroxide In ethanol; isopropyl alcohol	75%

4-sulfanylphenol (637-89-8) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(4-hydroxyphenylthio)-1-(thiophen-2-yl)-1-propanone

Conditions	Yield
In ethanol; water for 1h; Reflux;	70%

1,2,4-Triazole (288-88-0) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)-1-propanone (81234-93-7)

Conditions	Yield
In toluene for 7h; Reflux;	70%

3,5-dimethyl-1H-pyrazole (67-51-6) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(3,5-dimethyl-1H-pyrazol-1-yl)-1-(thiophen-2-yl)-1-propanone

Conditions	Yield
In water for 1h; Reflux;	69%

N-(4-iodophenyl)benzamide (52807-29-1) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → trans-1-[4-(benzoylamino)phenyl]-3-(2-thienyl)-1-propen-3-one

Conditions	Yield
With triethylamine; palladium diacetate In N,N-dimethyl-formamide at 140℃; for 0.5h; Heck reaction;	65%

1H-imidazole (288-32-4) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(1H-imidazole-1-yl)-1-(thiophen-2-yl)propan-1-one (1296877-16-1)

Conditions	Yield
In water for 1h; Reflux;	64%

1-(p-bromophenacyl)pyridinium bromide (17282-37-0) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 2-(4-bromophenyl)-6-(thiophen-2-yl)pyridine

Conditions	Yield
With ammonium acetate; acetic acid for 6h; Reflux;	63%

NH-pyrazole (288-13-1) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(1H-pyrazol-1-yl)-1-(thiophen-2-yl)-1-propanone

Conditions	Yield
In water for 1h; Reflux;	62%

p-tolylhydrazine hydrochloride (637-60-5) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 1-(4-methylphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole (40566-71-0)

Conditions	Yield
With sodium hydroxide In ethanol for 3h; Reflux;	62%

1-(2-(4-chlorophenyl)-2-oxoethyl)pyridinium bromide (26031-66-3) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridine

Conditions	Yield
With ammonium acetate; acetic acid for 6h; Reflux;	62%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + 3-amino-4-methyl-6-phenyl-pyrazolo[3,4-d]pyrimidine (115073-23-9, 1047724-08-2) → 4-methyl-2-phenyl-6-(2-thienyl)-7,8-dihydropyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidine

Conditions	Yield
at 200℃;	59%

Thiomorpholin (123-90-0) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-(thiomorpholin-4-yl)-1-(thiophen-2-yl)-1-propanone hydrochloride

Conditions	Yield
In water at 20℃; for 24h;	59%

Isobutyl 4-aminobenzoate (94-14-4) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → isobutyl 4-(3-oxo-3-(thiophen-2-yl)propylamino)benzoate

Conditions	Yield
In ethanol; water for 1h; Reflux;	58%

pyrrolidinedithiocarbamate (25769-03-3) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → S-(3-oxo-3-(thiophen-2-yl)propyl)pyrrolidine-1-carbodithioate

Conditions	Yield
In water at 20℃; for 24h;	57%

3-aminothieno<3,4:3',4'>benzopyran-4-one (41078-15-3) + 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) → 3-amino-1-(3-thien-2-yl-3-oxopropyl)thieno<3,4-c>coumarin

Conditions	Yield
With acetic acid In ethanol for 3h; Alkylation; Heating;	56.3%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + para-bromobenzenethiol (106-53-6) → 3-(4-bromophenylthio)-1-(thiophen-2-yl)-1-propanone (477859-21-5)

Conditions	Yield
In ethanol; water for 1h; Reflux;	56%

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride (5424-47-5) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 7,8-dimethyl-4-(thiophen-2-yl)-2,3-dihydro-1H-1,5-benzodiazepine

Conditions	Yield
In ethanol for 0.5h; Reflux;	56%

Upstream product

• 88-15-3 2-Acetylthiophene 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 506-59-2 N,N-dimethylammonium chloride 
• 50-00-0 formaldehyd 

Downstream Products

• 13196-35-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one 
• 1253196-01-8 1-(N-methylthiocarbamoyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole 
• 13669-05-1 1,4-bis(thiophen-2-yl)butane-1,4-dione 
• 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 
• 144221-02-3 2-phenyl-6-(thiophen-2-yl)pyridine 
• 1467081-71-5 2-(4-methoxyphenyl)-6-(thiophen-2-yl)-4H-1,3,2-oxathiaphosphorine-2-sulfide 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 446826-88-6 1-benzyl-4-hydroxy-4-(thiophen-2-yl)piperidin-3-ylthiophen-2-yl methanone 
• 497178-55-9 4-(thiophen-2-yl)-2,3-dihydro-1H-1,5-benzodiazepine 
• 40566-71-0 1-(4-methylphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole 
• 37571-26-9 1-(3-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole 
• 40566-73-2 1-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole 
• 91803-19-9 1-phenyl-3-(thiophen-2-yl)-4,5-dihydropyrazole 

Relevant articles and documents

AN IMPROVED PROCESS TO SYNTHESIZE 5-(3-PYRIDYL)-2,2'-BITHIOPHENE(SENSITIZER)

The present invention discloses an improved catalytic process for the synthesis of 5-(3-pyridyl)-2, 2'-bithiophene in high yield and purity.

Duloxetine hydrochloride salt of basic and duloxetine (by machine translation)

[Problem] to suppress toxic byproducts, and suppressing the formation of decomposition products of high purity optical isomers as well as the method for manufacturing a basic duloxetine hydrochloride duloxetine. [Solution] a basic manufacturing method of duloxetine, [...], potassium hydroxide and toluene in the presence of alcohol in the mixing step, and, by heating the reaction mixture obtained, comprising the step of distilling off the solvent in the reaction portion, a basic manufacturing method of duloxetine. [Drawing] no (by machine translation)

METHOD FOR PRODUCING DULOXETINE HYDROCHLORIDE

PROBLEM TO BE SOLVED: To provide a new method for producing (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine hydrochloride (general name: duloxetine hydrochloride) useful as an antidepressant. SOLUTION: In a method for producing duloxetine hydrochloride, a solution obtained by dissolving a crude product containing duloxetine hydrochloride in a dissolving solvent (a first dissolution step) and acetone are mixed (a mixing step), the duloxetine hydrochloride precipitated in the obtained mixed solution is temporarily dissolved (a second dissolution step), and then the duloxetine hydrochloride is precipitated. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT