2538-50-3

Basic information

• Product Name: 3-METHYLAMINO-1-PHENYLACETONE HYDROCHLORIDE
• Synonyms: 3-METHYLAMINO-1-PHENYLACETONE HYDROCHLORIDE;3-(METHYLAMINO)PROPIOPHENONE HCL;3-Methylaminopropiophenone;3-Methylamino-1-Phenyl-1-Acetone HCl;3-Methylaminophenylpropanone hydrochloride;3-Methylamino-1-phenylpropan-1-one hydrochloride;3-(Methylamino)-1-phenyl-1-propanone hydrochloride;1-(MethylaMino)-3-phenylpropan-2-one hydrochloride
• CAS NO: 2538-50-3
• Molecular Formula: C₁₀H₁₃NO*ClH
• Molecular Weight: 199.68
• EINECS: C10H14ClNO
• Mol File: 2538-50-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 139-141 °C(Solv: acetone (67-64-1))
• Boiling Point: 274.7°C at 760 mmHg
• Flash Point: 114.1°C
• Appearance: /
• Density: 1.002g/cm³
• Vapor Pressure: 0.00534mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-METHYLAMINO-1-PHENYLACETONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLAMINO-1-PHENYLACETONE HYDROCHLORIDE(2538-50-3)
• EPA Substance Registry System: 3-METHYLAMINO-1-PHENYLACETONE HYDROCHLORIDE(2538-50-3)

Safety Data

• Hazardous Substances Data: 2538-50-3(Hazardous Substances Data)

Usage

Uses

3-(Methylamino)-1-phenylpropan-1-one Hydrochloride can be used for nontoxic non-irritating wood preservative for toys or teaching appliances.

InChI:InChI=1/C10H13NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,11H,7-8H2,1H3

Synthetic route

formaldehyd (50-00-0) + methylamine hydrochloride (593-51-1) + acetophenone (98-86-2) → β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3)

Conditions	Yield
With hydrogenchloride In ethanol; water at 110℃; for 20h; Sealed tube;	70%
With hydrogenchloride In ethanol; water at 110℃; for 20h;	39.8%
With hydrogenchloride In ethanol at 110℃;
With toluene-4-sulfonic acid In ethanol at 110℃; for 20h;

3-(dimethylamino)propiophenone hydrochloride (879-72-1) + suitable amine → β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3)

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → (R)-N-methyl-3-phenyl-3-hydroxypropylamine (115290-81-8)

Conditions	Yield
With Rh[((R,R)-BenzP*)(cod)]SbF6; hydrogen; caesium carbonate; zinc(II) chloride In methanol at 20℃; under 19001.3 Torr; for 48h; Autoclave; enantioselective reaction;	93%
Multi-step reaction with 2 steps 1: potassium borohydride / tetrahydrofuran / 66 °C 2: sodium hydrogencarbonate / chloroform; water View Scheme

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → (S)-N-methyl-3-amino-1-phenyl-1-propanol (114133-37-8)

Conditions	Yield
With Rh[((S,S)-BenzP*)(cod)]SbF6; hydrogen; caesium carbonate; zinc(II) chloride In methanol at 20℃; under 19001.3 Torr; for 20h; Autoclave; enantioselective reaction;	92%
With hydrogen; potassium carbonate; [Rh{(SC,RP)-duanphos}(norbornadiene)]SbF6 In methanol at 20℃; under 7500.6 Torr; for 12h;	90%
With [Rh((S,S)-BenzP*)(cod)]SbF6; hydrogen; magnesium sulfate; potassium carbonate In ethyl acetate at 50℃; under 37503.8 Torr; for 1h; enantioselective reaction;	80%

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → 3-methylamino-1-phenylpropan-1-ol (42142-52-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h;	90%
With sodium tetrahydroborate In methanol at 20℃; for 1h;

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → 3-methylamino-1-phenyl-propan-1-ol; hydrochloride (57256-92-5)

Conditions	Yield
With potassium borohydride In tetrahydrofuran at 66℃;	82%

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → N-(3-hydroxy-3-phenylpropyl)-N-methylacetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 1 h / 20 °C 2: CH2Cl2 / 0.17 h / 0 °C View Scheme

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → (S)-N-(3-hydroxy-3-phenylpropyl)-N-methylacetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: Rh[((S,S)-BenzP*)(cod)]SbF6; zinc(II) chloride; caesium carbonate; hydrogen / methanol / 20 h / 20 °C / 19001.3 Torr / Autoclave 2: dichloromethane / 0.17 h / 0 °C View Scheme

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → FLUOXETINE (54910-89-3, 57226-07-0, 100568-02-3, 100568-03-4, 59333-67-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2.1: sodium hydride / dimethyl sulfoxide / 0.5 h / 55 °C / Inert atmosphere 2.2: 1 h / 90 °C View Scheme

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → 4-(3-(methylamino)-1-phenylpropyl)phenol (1254705-11-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 1 h / 20 °C 2: trifluoroacetic acid / 48 h / 20 °C View Scheme

β-Methylaminoethyl phenyl ketone hydrochloride (2538-50-3) → atomoxetine hydrochloride (82248-59-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium borohydride / tetrahydrofuran / 66 °C 2.1: sodium hydrogencarbonate / chloroform; water 3.1: ethyl acetate / 77 °C 3.2: pH 1 - 2 View Scheme

Upstream product

• 50-00-0 formaldehyd 
• 593-51-1 methylamine hydrochloride 
• 98-86-2 acetophenone 
• 879-72-1 3-(dimethylamino)propiophenone hydrochloride 

Downstream Products

• 56229-27-7 Methyl(2-methyl-3-oxo-1-butyl)(2-benzoylethyl)amin 
• 103756-12-3 3,3’-(methylazanediyl)bis(1-phenylpropan-1-one) 
• 21912-89-0 3-methylamino-1,1-diphenyl-propan-1-ol 
• 57256-92-5 3-methylamino-1-phenyl-propan-1-ol; hydrochloride 
• 82248-59-7 atomoxetine hydrochloride 
• 1254705-11-7 4-(3-(methylamino)-1-phenylpropyl)phenol 
• 54910-89-3 FLUOXETINE 
• 115290-81-8 (R)-N-methyl-3-phenyl-3-hydroxypropylamine 
• 114133-37-8 (S)-N-methyl-3-amino-1-phenyl-1-propanol 
• 42142-52-9 3-methylamino-1-phenylpropan-1-ol 
• 78994-02-2 2-Chloro-3-methyl-6-phenyl-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide 
• 56229-33-5 Methyl(2-methyl-2-benzoyl-1-propyl)(2-benzoylethyl)amin 
• 56229-29-9 Methyl(3-oxo-1-butyl)(2-benzoylethyl)amin 
• 56229-23-3 Methyl(2-benzoyl-1-propyl)(2-benzoylethyl)amin 

Relevant articles and documents

A model target anti-tumor medicament and its preparation method and application (by machine translation)

This invention relates to the targeting of antineoplastic eEF2K of a small molecule inhibitor, its formula (I), formula (II) the structure of the formula (III): Formula (I), formula (II) compound of the formula (III) structure and its pharmaceutically acceptable salt thereof can kill cancer cells, the healthy organism cells are not affected, to various tumor is markedly inhibited, in particular breast cancer, glioma, stomach cancer, liver cancer cells is markedly inhibited. (by machine translation)

ZnCl2-promoted asymmetric hydrogenation of β-secondary-amino ketones catalyzed by a P-chiral rh-bisphosphine complex

A new catalytic system has been developed for the asymmetric hydrogenation of β-secondary-amino ketones using a highly efficient P-chiral bisphosphine-rhodium complex in combination with ZnCl2 as the activator of the catalyst. The chiral γ-secondary-amino alcohols were obtained in 90-94% yields, 90-99% enantioselectivities, and with high turnover numbers (up to 2000 S/C; S/C = substrate/catalyst ratio). A mechanism for the promoting effect of ZnCl2 on the catalytic system has been proposed on the basis of NMR spectroscopy and HRMS studies. This method was successfully applied to the asymmetric syntheses of three important drugs, (S)-duloxetine, (R)-fluoxetine, and (R)-atomoxetine, in high yields and with excellent enantioselectivities.

PROCESS FOR THE PREPARATION OF N-MONOSUBSTITUTED β-AMINO ALCOHOLS

The invention relates to a process for the synthesis of N-monosubstituted β-amino alcohols of formula (I) and/or an addition salt of a proton acid, wherein R1 and R2 independently represent alkyl, cycloalkyl, aryl or aralkyl, each being optionally further substituted with alkyl, alkoxy and/or halogen via direct preparation of N-monosubstituted β-amino ketones of formula and its addition salts of proton acids, wherein R1and R2 are as defined above.