Product Name

  • Name

    Atomoxetine hydrochloride

  • EINECS 200-659-6
  • CAS No. 82248-59-7
  • Article Data28
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 167-169oC
  • Formula C17H22ClNO
  • Boiling Point 389 °C at 760 mmHg
  • Molecular Weight 291.821
  • Flash Point 164.1 °C
  • Transport Information
  • Appearance solid
  • Safety 22-24/25
  • Risk Codes 11-23/24/25-39/23/24/25
  • Molecular Structure Molecular Structure of 82248-59-7 (Atomoxetine hydrochloride)
  • Hazard Symbols F,T
  • Synonyms Benzenepropanamine,N-methyl-g-(2-methylphenoxy)-,hydrochloride, (R)-;Benzenepropanamine, N-methyl-g-(2-methylphenoxy)-, hydrochloride, (gR)- (9CI);(R)-(-)-N-Methyl-3-[(2-methylphenyl)oxy]-3-phenyl-1-aminopropane hydrochloride;(R)-(-)-Tomoxetine hydrochloride;(R)-N-Methyl-3-(2-methylphenoxy)-3-phenylpropylamine hydrochloride;(R)-Tomoxetine hydrochloride;Atomoxetine hydrochloride;LY 139603;Strattera;Tomoxetine hydrochloride;(3R)-N-Methyl-3-(2-methylphenoxy)-3-phenyl-1-propanamine hydrochloride (1:1);(3R)-N-méthyl-3-(2-méthylphénoxy)-3-phénylpropan-1-amine chlorhydrate;benzenepropanamine, N-methyl-γ-(2-methylphenoxy)-, (gammaR)-, hydrochloride;Atomoxetine HCL;
  • PSA 21.26000
  • LogP 4.91750

Synthetic route

(R)-tomoxetine
105314-52-1, 105314-53-2, 63940-51-2, 83015-26-3

(R)-tomoxetine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether99%
With hydrogenchloride In acetic acid butyl ester; water at 22 - 25℃; Product distribution / selectivity;99.8%
With hydrogenchloride In ethyl acetate at 12 - 18℃; Product distribution / selectivity;95%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

(R)-N-methyl-3-phenyl-3-hydroxypropylamine
115290-81-8

(R)-N-methyl-3-phenyl-3-hydroxypropylamine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux;
Stage #2: With hydrogenchloride In water pH=1 - 2;
Stage #3: With sodium hydroxide In water pH=11 - 12;		99%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium carbonate; copper(l) iodide In toluene at 148℃; for 21h; Ullmann type reaction; Heating / reflux;
Stage #2: With hydrogenchloride In water pH=1 - 2;
Stage #3: With sodium hydroxide In water pH=11 - 12;		94%
Stage #1: ortho-methylphenyl iodide; (R)-N-methyl-3-phenyl-3-hydroxypropylamine With potassium phosphate; copper(l) iodide In toluene for 24h; Ullmann type reaction; Heating / reflux;
Stage #2: With hydrogenchloride In water pH=1 - 2;
Stage #3: With sodium hydroxide In water pH=12 - 14;		82%
(R)-tomoxetine (S)-(+)-mandelate
83113-55-7

(R)-tomoxetine (S)-(+)-mandelate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: (R)-tomoxetine (S)-(+)-mandelate In ethyl acetate at 20℃; Heating / reflux;
Stage #2: With hydrogenchloride In acetic acid butyl ester at 15 - 20℃; for 2h; Product distribution / selectivity;		97%
Stage #1: (R)-tomoxetine (S)-(+)-mandelate With sodium hydroxide In water; ethyl acetate at 73 - 74℃; Heating / reflux;
Stage #2: With hydrogenchloride In water; ethyl acetate at 18 - 20℃; Product distribution / selectivity;		84%
Stage #1: (R)-tomoxetine (S)-(+)-mandelate In acetic acid butyl ester at 20℃; Heating / reflux;
Stage #2: With hydrogenchloride In acetic acid butyl ester; water at 18 - 20℃; for 1h; Product distribution / selectivity;		79.7%
-(-)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane
114446-47-8

-(-)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane

methylamine
74-89-5

methylamine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
In ethanol; water at 130℃; for 3h;95%
R-(-)-atomoxetine-S-(+)-mandelate

R-(-)-atomoxetine-S-(+)-mandelate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: R-(-)-atomoxetine-S-(+)-mandelate With sodium hydroxide In water at 40 - 45℃; for 0.166667h; Large scale;
Stage #2: With hydrogenchloride In water at 20℃; Large scale;		95%
C17H21NO*C8H8O3

C17H21NO*C8H8O3

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: C17H21NO*C8H8O3 With potassium carbonate In ethyl acetate pH=1 - 2;
Stage #2: With hydrogenchloride In tert-butyl methyl ether pH=1 - Ca. 2; Solvent;		92.2%
(-)-N-tert-butoxycarbonyl-N-methyl-3-phenyl-3-(2-methylphenoxy)propanamine
134619-78-6

(-)-N-tert-butoxycarbonyl-N-methyl-3-phenyl-3-(2-methylphenoxy)propanamine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol89%
With hydrogenchloride In ethanol Ambient temperature;88.7%
(S)-tomoxetine (S)-(+)-mandelate
872996-05-9

(S)-tomoxetine (S)-(+)-mandelate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: (S)-tomoxetine (S)-(+)-mandelate With water; sodium hydroxide In tert-butyl methyl ether for 1h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether at 0 - 5℃; for 2h; pH=2 - 3;		82.4%
(R)-N-methyl-3-phenyl-3-hydroxypropylamine
115290-81-8

(R)-N-methyl-3-phenyl-3-hydroxypropylamine

C7H7X

C7H7X

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: (R)-N-methyl-3-phenyl-3-hydroxypropylamine; C7H7X In ethyl acetate at 77℃;
Stage #2: With hydrogenchloride In water; acetone pH=1 - 2;		73%
C17H21NO*C8H8O3

C17H21NO*C8H8O3

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: C17H21NO*C8H8O3 With potassium carbonate In ethyl acetate
Stage #2: With hydrogenchloride In isopropyl alcohol		72.6%
ortho-cresol
95-48-7

ortho-cresol

(R)-N-methyl-3-phenyl-3-hydroxypropylamine
115290-81-8

(R)-N-methyl-3-phenyl-3-hydroxypropylamine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate Yield given. Multistep reaction;
ortho-cresol
95-48-7

ortho-cresol

methylamine
74-89-5

methylamine

3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate
51699-49-1

3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate

A

-(+)-tomoxetine hydrochloride
82857-39-4

-(+)-tomoxetine hydrochloride

B

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Stage #1: 3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate With 3 A molecular sieve; oxygen; (-)-sparteine; palladium diacetate In toluene at 80℃; under 760 Torr; for 36h;
Stage #2: methylamine With water In tetrahydrofuran at 65℃;
Stage #3: ortho-cresol With hydrogenchloride; triphenylphosphine; diethylazodicarboxylate In diethyl ether at -10 - 0℃;
...Expand
butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester
118856-08-9

butyric acid 2-ethoxycarbonyl-1-phenyl-ethyl ester

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C
2.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
3.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling
4.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
4.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
5.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
6.1: 99 percent / HCl / diethyl ether
View Scheme
(3S) ethyl β-butyryloxy-β-phenyl propionate
838841-85-3

(3S) ethyl β-butyryloxy-β-phenyl propionate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
2.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling
3.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
3.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
4.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
5.1: 99 percent / HCl / diethyl ether
View Scheme
Ethyl 3-hydroxy-3-phenylpropanoate
5764-85-2

Ethyl 3-hydroxy-3-phenylpropanoate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C
2.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C
3.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
4.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling
5.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
5.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
6.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
7.1: 99 percent / HCl / diethyl ether
View Scheme
Multi-step reaction with 3 steps
1.1: 85 percent / lithium aluminum hydride / tetrahydrofuran / 2 h
2.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C
3.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr
3.2: H2O / tetrahydrofuran / 65 °C
3.3: PPh3; DEAD; HCl (g) / diethyl ether / -10 - 0 °C
View Scheme
(S)-3-phenyl-1,3-propanediol
96854-34-1

(S)-3-phenyl-1,3-propanediol

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling
2.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
2.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
3.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
4.1: 99 percent / HCl / diethyl ether
View Scheme
benzaldehyde
100-52-7

benzaldehyde

SASRIN-maleidobenzoic acid resin

SASRIN-maleidobenzoic acid resin

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: tetrahydrofuran; hexane / 1 h / -78 °C
2.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C
3.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C
4.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C
5.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling
6.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
6.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
7.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
8.1: 99 percent / HCl / diethyl ether
View Scheme
(1S) 3-phenyl-3-hydroxypropyl methanesulfonate
115290-77-2

(1S) 3-phenyl-3-hydroxypropyl methanesulfonate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C
1.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C
2.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
3.1: 99 percent / HCl / diethyl ether
View Scheme
(R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate
115290-79-4

(R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C
2: 99 percent / HCl / diethyl ether
View Scheme
1-phenyl-1,3-propanediol
4850-49-1

1-phenyl-1,3-propanediol

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 95 percent / Et3N / CH2Cl2 / 0 h / -10 °C
2.1: O2; (-)-sparteine; 3 Angstroem sieves / Pd(OAc)2 / toluene / 36 h / 80 °C / 760 Torr
2.2: H2O / tetrahydrofuran / 65 °C
2.3: PPh3; DEAD; HCl (g) / diethyl ether / -10 - 0 °C
View Scheme
3-hydroxy-3-phenylpropanenitrile
73627-97-1, 121617-17-2, 132203-26-0, 17190-29-3

3-hydroxy-3-phenylpropanenitrile

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen, NH3 / Raney Ni / ethanol / 90 °C / p(NH3) = 30 psi and p(H2) = 170 psi
2: NaHCO3 / tetrahydrofuran
3: LiAlH4 / tetrahydrofuran / Heating
4: 1) DEAD, Ph3P
View Scheme
(1R)-3-amino-1-phenyl-1-propanol
138750-31-9

(1R)-3-amino-1-phenyl-1-propanol

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaHCO3 / tetrahydrofuran
2: LiAlH4 / tetrahydrofuran / Heating
3: 1) DEAD, Ph3P
View Scheme
((R)-3-Hydroxy-3-phenyl-propyl)-carbamic acid methyl ester

((R)-3-Hydroxy-3-phenyl-propyl)-carbamic acid methyl ester

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / tetrahydrofuran / Heating
2: 1) DEAD, Ph3P
View Scheme
(S)-N-methyl-3-amino-1-phenyl-1-propanol
114133-37-8

(S)-N-methyl-3-amino-1-phenyl-1-propanol

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / CH2Cl2 / 2 h / Heating
2: 84.4 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C
3: 88.7 percent / HCl gas / ethanol / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / CH2Cl2
2: Ph3P, DEAD / diethyl ether
3: 89 percent / HCl / ethanol
View Scheme
(S)-3-hydroxy-N-methyl-3-phenylpropanamide
76183-10-3, 134619-76-4

(S)-3-hydroxy-N-methyl-3-phenylpropanamide

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97.6 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating
2: 95 percent / CH2Cl2 / 2 h / Heating
3: 84.4 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C
4: 88.7 percent / HCl gas / ethanol / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / LiAlH4 / diethyl ether
2: 95 percent / CH2Cl2
3: Ph3P, DEAD / diethyl ether
4: 89 percent / HCl / ethanol
View Scheme
(-)-N-tert-butoxycarbonyl-N-methyl-3-phenyl-3-hydroxypropylamine
134619-77-5

(-)-N-tert-butoxycarbonyl-N-methyl-3-phenyl-3-hydroxypropylamine

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.4 percent / PPh3, diethyl azodicarboxylate / diethyl ether / 5 h / -10 °C
2: 88.7 percent / HCl gas / ethanol / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: Ph3P, DEAD / diethyl ether
2: 89 percent / HCl / ethanol
View Scheme
3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature
2: 95 percent / ethanol; H2O / 3 h / 130 °C
View Scheme
ortho-cresol
95-48-7

ortho-cresol

colloid/al platinum

colloid/al platinum

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature
2: 95 percent / ethanol; H2O / 3 h / 130 °C
View Scheme
ethyl (3R)-3-hydroxy-3-phenylpropionate
33401-74-0

ethyl (3R)-3-hydroxy-3-phenylpropionate

atomoxetine hydrochloride
82248-59-7

atomoxetine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / H2O
2: 98 percent / LiAlH4 / diethyl ether
3: 95 percent / CH2Cl2
4: Ph3P, DEAD / diethyl ether
5: 89 percent / HCl / ethanol
View Scheme

Atomoxetine hydrochloride Specification

The Atomoxetine hydrochloride, with the CAS registry number 82248-59-7, has the systematic name of (3R)-N-methyl-3-(2-methylphenoxy)-3-phenylpropan-1-amine hydrochloride (1:1). And the molecular formula of this chemical is C17H22ClNO. What's more, it should be stored at 2-8°C. In addition, while dealing with this chemical, you should not breathe dust and then try to avoid contacting with skin and eyes. And it is often used as norepinephrine reuptake inhibitor.

The physical properties of Atomoxetine hydrochloride are as following: (1)ACD/LogP: 3.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.2; (4)ACD/LogD (pH 7.4): 0.71; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.19; (8)ACD/KOC (pH 7.4): 3.91; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 12.47 Å2; (13)Flash Point: 164.1 °C; (14)Enthalpy of Vaporization: 63.82 kJ/mol; (15)Boiling Point: 389 °C at 760 mmHg; (16)Vapour Pressure: 2.95E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.O(c1ccccc1C)[C@@H](c2ccccc2)CCNC
(2)InChI: InChI=1/C17H21NO.ClH/c1-14-8-6-7-11-16(14)19-17(12-13-18-2)15-9-4-3-5-10-15;/h3-11,17-18H,12-13H2,1-2H3;1H/t17-;/m1./s1
(3)InChIKey: LUCXVPAZUDVVBT-UNTBIKODBW

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