Product Name

  • Name

    (S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one

  • EINECS 617-655-9
  • CAS No. 850222-40-1
  • Article Data541
  • CAS DataBase
  • Density 1.012 g/cm3
  • Solubility
  • Melting Point
  • Formula C13H19NO2
  • Boiling Point 315.8 °C at 760 mmHg
  • Molecular Weight 221.299
  • Flash Point 144.8 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 850222-40-1 ((S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one)
  • Hazard Symbols
  • Synonyms (S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone;(S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one;
  • PSA 29.54000
  • LogP 2.07560

Synthetic route

(S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one (2R,3R)-O,O'-dibenzoyltartrate
850222-41-2

(S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one (2R,3R)-O,O'-dibenzoyltartrate

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
With diethylamine In tert-butyl methyl ether at 20 - 25℃; for 1.5h;96.5%
With diethylamine In tert-butyl methyl ether at 20℃; for 3h; Product distribution / selectivity;
With ammonia; water In 2-methyltetrahydrofuran for 0.5h; Product distribution / selectivity;
With diethylamine In tert-butyl methyl ether
formaldehyd
50-00-0

formaldehyd

1-(3-methoxyphenyl)propan-1-one
37951-49-8

1-(3-methoxyphenyl)propan-1-one

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
With hydrogenchloride; L-proline In ethanol; water for 16h; Reflux; Inert atmosphere;78%
...Expand
3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one
197145-37-2

3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1-one

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone; methanol
2: diethylamine / tert-butyl methyl ether
View Scheme
1-(3-methoxyphenyl)propan-2-one
3027-13-2

1-(3-methoxyphenyl)propan-2-one

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid
2: acetone; methanol
3: diethylamine / tert-butyl methyl ether
View Scheme
formaldehyd
50-00-0

formaldehyd

1-(3-methoxyphenyl)propan-1-one
37951-49-8

1-(3-methoxyphenyl)propan-1-one

dimethyl amine
124-40-3

dimethyl amine

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

Conditions
ConditionsYield
With L-proline In ethanol at 77℃; for 36h; Temperature; Solvent; Mannich Aminomethylation;306.2 g
...Expand
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol
809282-20-0

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol

Conditions
ConditionsYield
Stage #1: (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone; ethylmagnesium bromide In tetrahydrofuran at 15℃; for 4h; Grignard Reaction;
Stage #2: With ammonium bisulphate; water In tetrahydrofuran at 5℃; Product distribution / selectivity;		99%
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol
809282-20-0

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol

Conditions
ConditionsYield
Stage #1: ethyl bromide With magnesium In diethyl ether at 35℃; for 2.5h;
Stage #2: (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone In diethyl ether at 10 - 15℃; for 2h; Grignard Reaction;
Stage #3: With ammonium bisulphate; water In diethyl ether at 5℃; Product distribution / selectivity;		98%
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(2SS,3RS)-[3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol]-dimethylamine

(2SS,3RS)-[3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol]-dimethylamine

Conditions
ConditionsYield
Stage #1: (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 10 - 15℃; for 2h; Grignard Reaction;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 5℃;		71%
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol
809282-20-0

(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methyl pentan-3-ol

Conditions
ConditionsYield
Stage #1: (2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone; ethylmagnesium chloride In tetrahydrofuran at 2 - 25℃; for 3.83333h; Grignard Reaction;
Stage #2: With water; acetic acid In tetrahydrofuran at 20℃; for 0.5h;
Stage #3: With ammonia; water In tetrahydrofuran at 20℃; for 0.166667h;
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

(βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine
175591-22-7

(βR,γR)-γ-ethyl-N,N,β-trimethyl-3-methoxybenzenepropanamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 20 °C / Inert atmosphere
View Scheme
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

tapentadol hydrochloride

tapentadol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 20 °C / Inert atmosphere
4.1: methanesulfonic acid; DL-methionine / 72 h / 80 °C
4.2: pH 10 - 12
5.1: hydrogenchloride / diethyl ether / 4 h
View Scheme
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

tapentadol
175591-23-8

tapentadol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 20 °C / Inert atmosphere
4.1: methanesulfonic acid; DL-methionine / 72 h / 80 °C
4.2: pH 10 - 12
View Scheme
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

(R)-3-(3-methoxyphenyl)-N,N,2-trimethylpent-3-en-1-amine

(R)-3-(3-methoxyphenyl)-N,N,2-trimethylpent-3-en-1-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
View Scheme
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

(R,R)-tapentadol-(PABA tert-butyl ester) carbamate
1314003-88-7

(R,R)-tapentadol-(PABA tert-butyl ester) carbamate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 20 °C / Inert atmosphere
4.1: methanesulfonic acid; DL-methionine / 72 h / 80 °C
4.2: pH 10 - 12
5.1: toluene / Reflux
View Scheme
(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone
850222-40-1

(2S)-3-dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone

(R,R)-tapentadol-PABA carbamate trifluoroacetate
1314003-30-9

(R,R)-tapentadol-PABA carbamate trifluoroacetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: diethyl ether; tetrahydrofuran / 2 h / 10 - 15 °C
1.2: 5 °C
2.1: hydrogenchloride / water / 5 h / 55 °C
2.2: 20 °C / pH 12
3.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / ethanol; water / 20 °C / Inert atmosphere
4.1: methanesulfonic acid; DL-methionine / 72 h / 80 °C
4.2: pH 10 - 12
5.1: toluene / Reflux
6.1: 1 h / 20 °C
View Scheme

(S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone Specification

The systematic name of 1-Propanone,3-(dimethylamino)-1-(3-methoxyphenyl)-2-methyl-, (2S)- is (2S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methyl-propan-1-one. With the CAS registry number 850222-40-1, it is also named as (S)-3-Dimethylamino-1-(3-methoxyphenyl)-2-methyl-1-propanone. In addition, its molecular formula is C13H19NO2 and its molecular weight is 221.30.

The other characteristics of 1-Propanone,3-(dimethylamino)-1-(3-methoxyphenyl)-2-methyl-, (2S)- can be summarized as: (1)ACD/LogP: 2.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 7.4): 0.79; (4)#H bond acceptors: 3; (5)#H bond donors: 0; (6)#Freely Rotating Bonds: 5; (7)Polar Surface Area: 29.54 Å2; (8)Index of Refraction: 1.508; (9)Molar Refractivity: 65.17 cm3; (10)Molar Volume: 218.6 cm3; (11)Polarizability: 25.83×10-24cm3; (12)Surface Tension: 34.8 dyne/cm; (13)Density: 1.012 g/cm3; (14)Flash Point: 144.8 °C; (15)Enthalpy of Vaporization: 55.7 kJ/mol; (16)Boiling Point: 315.8 °C at 760 mmHg; (17)Vapour Pressure: 0.000428 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: CC(CN(C)C)C(=O)c1cccc(c1)OC
(2)InChI: InChI=1/C13H19NO2/c1-10(9-14(2)3)13(15)11-6-5-7-12(8-11)16-4/h5-8,10H,9H2,1-4H3/t10-/m0/s1
(3)InChIKey: YHCVGGJYRMYIGG-JTQLQIEIBN
(4)Std. InChI: InChI=1S/C13H19NO2/c1-10(9-14(2)3)13(15)11-6-5-7-12(8-11)16-4/h5-8,10H,9H2,1-4H3/t10-/m0/s1
(5)Std. InChIKey: YHCVGGJYRMYIGG-JTQLQIEISA-N

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