• Name

  1-[2-Amino-1-(4-methoxyphenyl)-ethyl]-cyclohexanol hydrochloride

• EINECS 603-392-7
• CAS No. 130198-05-9
• Article Data9
• CAS DataBase
• Density
• Solubility
• Melting Point 172-180 °C
• Formula C₁₅H₂₄ClNO₂
• Boiling Point 394.6 °C at 760 mmHg
• Molecular Weight 285.814
• Flash Point 192.5 °C
• Transport Information
• Appearance White crystalline powder
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Cyclohexanol,1-[2-amino-1-(4-methoxyphenyl)ethyl]-, hydrochloride (9CI);Cyclohexanol,1-[2-amino-1-(4-methoxyphenyl)ethyl]-, hydrochloride, (?à)-;1-[2-Amino-1-(p-methoxyphenyl)ethyl]cyclohexanol hydrochloride;N,N-Didesmethylvenlafaxine Hydrochloride;(1-[2-amlno-1-(4-methoxyphenyl)ethyl]cyciohexanol);1-[2-Amino-1-(4-Methyoxyphenyl)ethyl] Cyclohexanol.HCL;
• PSA 55.48000
• LogP 3.93500

Synthetic route

93413-76-4

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol With dimethylsulfide borane complex In dichloromethane at 85℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water Reagent/catalyst; Solvent; Temperature;	97.5%
With hydrogenchloride; hydrogen In 1,4-dioxane; ethanol at 60℃; under 2625.26 Torr; for 18h; Flow reactor;	93%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; ethanol at 20℃; under 2625.26 Torr; for 6h; Product distribution / selectivity;	91%

93413-77-5, 272788-06-4, 273720-73-3

N,N-didesmethylvenlafaxine

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate; isopropyl alcohol at 5 - 10℃; for 0.666667 - 1h; Product distribution / selectivity;	75%
With hydrogenchloride In tert-butyl methyl ether at 0℃; for 0.25h;	52.3%

isopropanolic HCl

isopropanolic HCl

93413-76-4

1-[cyano(4-methoxyphenyl)methyl]cyclohexanol

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

Conditions

Conditions	Yield
With ammonium hydroxide; aluminum nickel In methanol; ethyl acetate

108-94-1

cyclohexanone

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - -65 °C 1.2: 2 h / -78 - -65 °C 2.1: cobalt(II) chloride; sodium tetrahydroborate / methanol / 2 h / 20 - 35 °C 3.1: hydrogenchloride / tert-butyl methyl ether / 0.25 h / 0 °C View Scheme

104-47-2

p-methoxybenzylnitrile

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - -65 °C 1.2: 2 h / -78 - -65 °C 2.1: cobalt(II) chloride; sodium tetrahydroborate / methanol / 2 h / 20 - 35 °C 3.1: hydrogenchloride / tert-butyl methyl ether / 0.25 h / 0 °C View Scheme

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

149289-29-2

N,N-Didesmethyldesvenlafaxine

Conditions

Conditions	Yield
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With sodium sulfide hydrate In 1-methyl-pyrrolidin-2-one at 20 - 185℃; Stage #2: With succinic acid In 1-methyl-pyrrolidin-2-one; water at 10 - 90℃; pH=10 - 11;	91%
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With sodium sulfide In 1-methyl-pyrrolidin-2-one at 185℃; for 8h; Stage #2: With succinic acid In 1-methyl-pyrrolidin-2-one; water at 25 - 90℃; Product distribution / selectivity;	80%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 210℃; for 5.5h;

50-00-0

formaldehyd

64-18-6

formic acid

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

93413-69-5

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

Conditions

Conditions	Yield
With sodium hydroxide In water for 20 - 24h; Product distribution / selectivity; Heating / reflux;	64.56%

...Expand

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

93413-69-5

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

Conditions

Conditions	Yield
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With sodium hydroxide; formaldehyd; formic acid In water at 20℃; for 5h; Heating / reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=12;
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With formaldehyd; formic acid; triethylamine In water at 20℃; for 0.25h; Stage #2: With sodium hydroxide In water at 15 - 20℃; pH=10 - 11; Product distribution / selectivity;

50-00-0

formaldehyd

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

99300-78-4

venlafaxine hydrochloride

Conditions

Conditions	Yield
Stage #1: formaldehyd; 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With formic acid In water at 97 - 99℃; for 16h; Stage #2: With hydrogenchloride In isopropyl alcohol at 10℃; for 1 - 2h; pH=2.0;

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

99300-78-4

venlafaxine hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With formic acid; hexamethylenetetramine In water at 20 - 102℃; for 0.25h; Stage #2: With sodium hydroxide In water at 15 - 20℃; pH=10 - 11; Product distribution / selectivity;

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

93413-77-5, 272788-06-4, 273720-73-3

N,N-didesmethylvenlafaxine

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 0.25h; Product distribution / selectivity;
With sodium methylate In methanol at 20℃; for 0.5h; Product distribution / selectivity;

50-00-0

formaldehyd

130198-05-9

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

93413-69-5

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

Conditions

Conditions	Yield
With formic acid In ethanol; water at 100℃; for 48h; Flow reactor;
With formic acid; sodium hydroxide at 85 - 90℃; Temperature;	107.44 g

1-[2-Amino-1-(4-methoxyphenyl)-ethyl]-cyclohexanol hydrochloride Chemical Properties