1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol
venlafaxine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; ethyl acetate at 68 - 73℃; pH=2.5; | 95% |
With hydrogenchloride In ethyl acetate; isopropyl alcohol for 1h; Reflux; | 87% |
With hydrogenchloride In isopropyl alcohol at 5 - 80℃; for 1.5 - 2h; Product distribution / selectivity; | 75% |
formaldehyd
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride With sodium hydroxide In methanol at 0 - 5℃; for 0.5h; pH=9 - 9.5; Stage #2: formaldehyd With formic acid In water at 20 - 100℃; for 14 - 15h; Stage #3: With hydrogenchloride; sodium hydroxide more than 3 stages; | 95% |
formaldehyd
venlafaxine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; formic acid In dichloromethane; water pH=1; Reflux; | 94.2% |
Stage #1: formaldehyd; 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hemisulfate With formic acid In water Reflux; Stage #2: With hydrogenchloride In water | 93.8% |
formaldehyd
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: [RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid; formaldehyd With formic acid In water at 98℃; for 20h; Stage #2: With hydrogenchloride In isopropyl alcohol at 10 - 60℃; for 2 - 2.5h; pH=1 - 1.5; | 84% |
Stage #1: [RS]-1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol acetic acid; formaldehyd With formic acid In water at 90 - 98℃; for 19h; Stage #2: With sodium hydroxide In water at 5℃; Stage #3: With hydrogenchloride In i-Amyl alcohol pH=~ 2; |
formaldehyd
formic acid
1-[cyano(4-methoxyphenyl)methyl]cyclohexanol
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 5℃; for 1 - 1.5h; Stage #2: 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol In tetrahydrofuran at 0 - 40℃; for 5 - 6.5h; Stage #3: formaldehyd; formic acid With hydrogenchloride Product distribution / selectivity; more than 3 stages; | 78.25% |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-[(4-methoxyphenyl)(dimethylamino)carbonylmethyl]cyclohexanol With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 0 - 2℃; for 3 - 4h; Stage #2: With sodium hydroxide In water; toluene at 0 - 30℃; for 0.25 - 0.5h; Stage #3: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 25℃; for 2h; | |
In tetrahydrofuran at 0℃; for 1h; |
formaldehyd
1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride
venlafaxine hydrochloride
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; |
1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride
venlafaxine hydrochloride
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; |
formaldehyd
N,N-didesmethylvenlafaxine
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: formaldehyd; N,N-didesmethylvenlafaxine With formic acid In water at 95 - 100℃; Stage #2: With sodium hydroxide In water pH=> 12; Stage #3: With hydrogenchloride In water at 25 - 30℃; | |
Stage #1: formaldehyd; N,N-didesmethylvenlafaxine With formic acid In water Stage #2: With hydrogenchloride In isopropyl alcohol |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: formic acid / water / 22 h / 100 °C / Large scale reaction 2: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction View Scheme |
cyclohexanone
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 2 h / 0 - 5 °C / Large scale reaction 1.2: 4 h / 0 - 5 °C / Large scale reaction 2.1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction 3.1: formic acid / water / 22 h / 100 °C / Large scale reaction 4.1: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction View Scheme |
1-[cyano(4-methoxyphenyl)methyl]cyclohexanol
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction 2: formic acid / water / 22 h / 100 °C / Large scale reaction 3: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen / ethyl acetate / 40 °C / 2250.23 - 3000.3 Torr 2: sulfuric acid / ethyl acetate / 2 h / 0 - 10 °C 3: formic acid; hydrogenchloride / water; dichloromethane / pH 1 / Reflux View Scheme |
p-methoxybenzylnitrile
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 2 h / 0 - 5 °C / Large scale reaction 1.2: 4 h / 0 - 5 °C / Large scale reaction 2.1: hydrogen / 3 h / 55 °C / 7500.75 - 9000.9 Torr / Large scale reaction 3.1: formic acid / water / 22 h / 100 °C / Large scale reaction 4.1: hydrogenchloride / water; isopropyl alcohol; toluene / 2 h / 0 - 5 °C / pH 3 - 4.5 / Large scale reaction View Scheme |
venlafaxine hydrochloride
1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol
Conditions | Yield |
---|---|
With sodium hydroxide In water | 98.9% |
With sodium hydroxide In water pH=12 - 13; | |
With sodium hydroxide In dichloromethane; water at 25 - 35℃; pH=12 - 13; |
venlafaxine hydrochloride
O-desmethylvenlafaxine
Conditions | Yield |
---|---|
Stage #1: venlafaxine hydrochloride With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 0 - 140℃; for 7h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 35℃; pH=2 - 3; | 92% |
Stage #1: venlafaxine hydrochloride With sodium hydride; ethanethiol In N,N-dimethyl-formamide at 0 - 140℃; Stage #2: With hydrogenchloride; pyrographite In water; N,N-dimethyl-formamide at 35℃; for 0.5h; Industry scale; Stage #3: With sodium hydroxide In water pH=8.5 - 9; Industry scale; | 92% |
Stage #1: venlafaxine hydrochloride With potassium tert-butylate; ethane-1,2-dithiol In decaethylene glycol at 25 - 135℃; for 24 - 28h; Stage #2: With hydrogenchloride; water In decaethylene glycol at 25 - 30℃; Stage #3: With ammonia In water pH=> 9.5; Product distribution / selectivity; | 84% |
venlafaxine hydrochloride
O-desvenlafaxine hydrochloride
Conditions | Yield |
---|---|
With methanesulfonic acid; L-methionine Large scale; | 88.5% |
6-(benzyloxycarbonylamino)hexanoic acid
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 6-(benzyloxycarbonylamino)hexanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Stage #2: venlafaxine hydrochloride In dichloromethane at 45℃; for 6h; | 77.8% |
Stage #1: 6-(benzyloxycarbonylamino)hexanoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Stage #2: venlafaxine hydrochloride In dichloromethane at 20℃; for 3h; | 77.8% |
(2S,3S)-di-4-toluoyltartaric acid
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Stage #1: venlafaxine hydrochloride With sodium hydroxide In water; ethyl acetate for 0.25h; Stage #2: (2S,3S)-di-4-toluoyltartaric acid In methanol; ethyl acetate at 0 - 65℃; for 3.33333h; Heating / reflux; | n/a |
venlafaxine hydrochloride
desvenlafaxine succinate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / pH 12 - 13 2.1: sodium thiophenolate / N,N-dimethyl-formamide / 150 - 160 °C 2.2: 0.5 h / 25 - 35 °C / pH 3.5 3.1: water; acetone / 57 - 63 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / dichloromethane; water / 25 - 35 °C / pH 12 - 13 2.1: sodium thiophenolate / N,N-dimethyl-formamide / 155 °C 2.2: 2 h / 25 - 35 °C / pH 3.5 2.3: 0.5 h / pH 9 - 9.5 3.1: water; acetone / 0 - 60 °C / Inert atmosphere View Scheme |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
In methanol for 35.33h; Irradiation; | 850 mg |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux View Scheme |
venlafaxine hydrochloride
(R)-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux 3.1: sodium hydroxide / water View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; ethyl acetate / 0.25 h 1.2: 3.33 h / 0 - 65 °C / Heating / reflux 2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h View Scheme |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux 3.1: sodium hydroxide / water 4.1: tetrahydrofuran View Scheme |
venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux View Scheme |
venlafaxine hydrochloride
(S)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux 3.1: sodium hydroxide / water View Scheme |
venlafaxine hydrochloride
(+)-Venlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water 2.1: tetrahydrofuran / 0.5 h / Resolution of racemate; Reflux 2.2: 0.5 h / Resolution of racemate; Reflux 3.1: sodium hydroxide / water 4.1: hydrogenchloride / ethyl acetate View Scheme |
venlafaxine hydrochloride
(R)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water; ethyl acetate / 0.25 h 1.2: 3.33 h / 0 - 65 °C / Heating / reflux 2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h 3.1: lithium diphenylphosphide / tetrahydrofuran / 24 h / 50 °C 3.2: 0.25 h / 22 °C 3.3: pH 9.5 View Scheme |
venlafaxine hydrochloride
(-)-O-desmethylvenlafaxine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide / water; ethyl acetate / 0.25 h 1.2: 3.33 h / 0 - 65 °C / Heating / reflux 2.1: sodium hydroxide / tert-butyl methyl ether; water / 0.25 h 3.1: lithium diphenylphosphide / tetrahydrofuran / 24 h / 50 °C 3.2: 0.25 h / 22 °C 3.3: pH 9.5 4.1: hydrogenchloride / water / 1 h / 0 - 60 °C View Scheme |
Molecular structure of Venlafaxine hydrochloride (CAS NO.99300-78-4) is:
Product Name: Venlafaxine hydrochloride
CAS Registry Number: 99300-78-4
IUPAC Name: 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-olhydrochloride
Molecular Weight: 313.86272 [g/mol]
Molecular Formula: C17H28ClNO2
H-Bond Donor: 2
H-Bond Acceptor: 3
Melting Point: 207-209 °C
Flash Point: 194.2 °C
Enthalpy of Vaporization: 68.34 kJ/mol
Boiling Point: 397.6 °C at 760 mmHg
Vapour Pressure: 4.92E-07 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;Medicine intermediate;Antidepressant;APIs;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Serotonin receptor
Venlafaxine hydrochloride (CAS NO.99300-78-4) can be used as a selective serotonin noradrenaline reuptake inhibitor and also used as an antidepressant. And, it is used primarily for the treatment of major depression in adults.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 1071ug/kg (1.071mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 211, 1997. |
man | TDLo | oral | 32mg/kg/9W-I (32mg/kg) | BEHAVIORAL: HEADACHE BEHAVIORAL: WITHDRAWAL | Medical Journal of Australia. Vol. 169, Pg. 91, 1998. |
women | LDLo | oral | 168mg/kg (168mg/kg) | BEHAVIORAL: COMA CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Medical Journal of Australia. Vol. 169, Pg. 445, 1998. |
women | LDLo | oral | 235mg/kg/12D- (235mg/kg) | LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" GASTROINTESTINAL: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | Journal of Analytical Toxicology. Vol. 20, Pg. 266, 1996. |
women | TDLo | oral | 94500ug/kg/9W (94.5mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Annals of Pharmacotherpy. Vol. 33, Pg. 1009, 1999. |
women | TDLo | oral | 315mg/kg/30W- (315mg/kg) | BEHAVIORAL: WITHDRAWAL GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Medical Journal of Australia. Vol. 169, Pg. 91, 1998. |
women | TDLo | oral | 360mg/kg/17W- (360mg/kg) | BEHAVIORAL: WITHDRAWAL SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Medical Journal of Australia. Vol. 169, Pg. 91, 1998. |
Hazard Codes: Xi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
Venlafaxine hydrochloride , its cas register number is 99300-78-4. It also can be called (+/-)-1-(alpha-((Dimethylamino)methyl)-p-methoxybenzyl)cyclohexanol hydrochloride ; (RS)-1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride ; Effexor .It is a white crystalline powder.
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