2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
With sodium acetate In ethanol for 1h; Reflux; | 99.5% |
With sodium acetate In Isopropyl acetate | 99% |
With sodium acetate In ethanol for 1h; Reflux; | 95% |
2-(2-methoxynaphthalen-8-yl)acetaldehyde oxime
agomelatine
Conditions | Yield |
---|---|
With hydrogen; acetic anhydride In tetrahydrofuran at 50℃; under 7500.75 Torr; for 6h; Autoclave; Inert atmosphere; | 98% |
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
Stage #1: N,N-dibenzyl-2-(7-methoxynaphthalen-1-yl)ethanamine With 20% palladium hydroxide-activated charcoal; hydrogen In ethanol; water; ethyl acetate under 3750.38 Torr; for 30h; Autoclave; Stage #2: acetic anhydride With sodium acetate for 4h; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 6h; Concentration; Temperature; | 97.5% |
With sodium acetate In ethanol at 65℃; Green chemistry; | 92% |
With triethylamine In toluene at 20 - 30℃; | 90% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 5℃; | 95% |
In pyridine | 92% |
With pyridine for 0.5h; Product distribution / selectivity; Cooling with ice; | 92% |
dimethyl sulfate
N-[2-(7-Hydroxy-1-naphthyl)ethyl]-acetamide
agomelatine
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 5h; Reflux; | 94.5% |
1-(2-nitroethyl)-7-methoxynaphthalene
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen In water; ethyl acetate at 20℃; | 92% |
1-[2-(7-methoxynahthalen-1-yl)-ethyl]-2λ5-triaz-1-en-2-yne
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In water; ethyl acetate at 20℃; | 92% |
N-[2-(7-methoxy-3,4-dihydro-naphthalen-1-yl)ethyl]acetamide
agomelatine
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; | 91.8% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 4h; Product distribution / selectivity; Reflux; | 90% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; Product distribution / selectivity; | 80% |
2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride
acetyl chloride
agomelatine
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 2h; | 91% |
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride With triethylamine In dichloromethane at 25 - 35℃; for 0.5h; Stage #2: acetyl chloride In dichloromethane at 10 - 20℃; for 1h; | 90% |
With potassium carbonate In chloroform; water for 0.5h; Ambient temperature; | 89% |
With potassium carbonate In chloroform; water at 0℃; | |
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride With potassium carbonate In water; ethyl acetate at 20℃; Schotten-Baumann reaction; Stage #2: acetyl chloride In water; ethyl acetate at 0 - 20℃; for 1h; Schotten-Baumann reaction; |
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
With sodium acetate In methanol Reflux; | 91% |
With sodium acetate In methanol Reflux; | 91% |
With sodium acetate In methanol Reflux; | 91% |
Conditions | Yield |
---|---|
With hydrogen; Raney nickel In ethanol; water at 70℃; under 22502.3 Torr; | 89% |
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr; | 89% |
With hydrogen In ethanol; water at 70℃; under 22502.3 Torr; for 1h; | 89% |
With hydrogen In ethanol at 60℃; under 37503.8 Torr; for 4h; | |
Stage #1: (7-methoxy-1-naphthyl)acetonitrile With hydrogen; sodium hydroxide In methanol; water at 30℃; under 3000.3 Torr; Stage #2: acetic anhydride In methanol at 15 - 25℃; |
Conditions | Yield |
---|---|
With sodium acetate In ethanol; acetic anhydride at 25℃; for 1h; Temperature; | 88.1% |
agomelatine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; ammonium acetate; magnesium In ethanol for 16h; | 87% |
N-[2-(1-hydroxyl-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]-acetamide
agomelatine
Conditions | Yield |
---|---|
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h; | 85% |
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 40℃; for 5h; | |
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate; water / 2 h / 20 °C 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 20 °C View Scheme |
2-(2-(7-methoxynaphthalen-1-yl)ethyl) isoindoline-1,3-dione
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
Stage #1: 2-(2-(7-methoxynaphthalen-1-yl)ethyl) isoindoline-1,3-dione With hydrazine hydrate In methanol; dichloromethane at 30℃; for 14h; Stage #2: acetic anhydride With triethylamine In methanol; dichloromethane; toluene at 25℃; for 0.333333h; | 85% |
agomelatine
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel dichloride at 20℃; for 0.5h; Sealed tube; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In 1,4-dioxane at 95 - 98℃; for 22h; | 76.3% |
acetic anhydride
2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate
agomelatine
Conditions | Yield |
---|---|
Stage #1: 2-(7-methoxynaphthalen-1-yl)ethyl methanesulphonate With ammonia In water; acetonitrile at 110℃; for 3h; Stage #2: acetic anhydride With sodium acetate for 1h; | 74% |
N-[2-(4-chloro-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
agomelatine
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux; | 68% |
N-[2-(4-bromo-7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
agomelatine
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol for 3h; Reflux; | 68% |
(E)-7-methoxy-1-(2-nitrovinyl)naphthalene
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; acetic acid | 65% |
Conditions | Yield |
---|---|
With acetic anhydride In ethanol at 20℃; for 1h; | 61% |
N-[2-(7-methoxy-1,2-dihydro-1-naphthyl)ethyl]acetamide
agomelatine
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 48h; | 48% |
acetic anhydride
agomelatine
Conditions | Yield |
---|---|
Stage #1: 1-[2-(2,5-dioxopyrrolidin-1-yl)ethyl]-7-methoxynaphthalen-2-yl propane-1-sulphonate With palladium 10% on activated carbon; ammonium acetate; magnesium In methanol at 30℃; for 12h; Stage #2: acetic anhydride With sodium acetate; sodium hydroxide In ethanol; water for 1h; Sealed tube; | 37% |
2-(7-methoxynaphth-1-yl)ethylamine
agomelatine
Conditions | Yield |
---|---|
With sheep pineal supernatant (serotonin-N-acetyl transferase); Pargyline In phosphate buffer at 37℃; for 0.166667h; pH=6.8; Enzyme kinetics; |
2-(7-methoxynaphthalen-1-yl)acetic acid
agomelatine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / CHCl3 2: aq. NH4OH / diethyl ether / 0 °C 3: AlH4 / diethyl ether 4: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: thionyl chloride / CHCl3 2: aq. NH4OH / diethyl ether / 0 °C 3: (CF3CO)2O / tetrahydrofuran / 0 °C 4: H2, HCl / Ni Raney / diethyl ether 5: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane / 2 h / Reflux 2.1: ammonia / ethyl acetate; water / Cooling with ice 3.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice 4.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave 5.1: pyridine / 40 °C 5.2: 20 °C / Cooling with ice View Scheme |
2-(2-methoxynaphthalen-8-yl)acetamide
agomelatine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlH4 / diethyl ether 2: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: (CF3CO)2O / tetrahydrofuran / 0 °C 2: H2, HCl / Ni Raney / diethyl ether 3: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice 2.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave 3.1: pyridine / 40 °C 3.2: 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C 2.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr 2.2: 1 h / 50 - 55 °C 3.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C 3.2: 35 - 40 °C View Scheme |
(7-methoxy-1-naphthyl)acetonitrile
agomelatine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2, HCl / Ni Raney / diethyl ether 2: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave 2.1: pyridine / 40 °C 2.2: 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr 1.2: 1 h / 50 - 55 °C 2.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C 2.2: 35 - 40 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: ammonia; hydrogen / methanol / 15 - 55 °C / 3750.38 Torr / Autoclave 1.2: 1 h / 0 - 5 °C 2.1: triethylamine / dichloromethane / 0.5 h / 25 - 35 °C 2.2: 1 h / 10 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: ammonia; hydrogen / ethanol / 24 h / 30 - 40 °C / 2250.23 - 3000.3 Torr / Autoclave 2: triethylamine / toluene / 0.5 h / 0 - 30 °C View Scheme |
(7-methoxy-1-naphthyl)acetic acid chloride
agomelatine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. NH4OH / diethyl ether / 0 °C 2: AlH4 / diethyl ether 3: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: aq. NH4OH / diethyl ether / 0 °C 2: (CF3CO)2O / tetrahydrofuran / 0 °C 3: H2, HCl / Ni Raney / diethyl ether 4: K2CO3 / H2O; CHCl3 / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: ammonia / ethyl acetate; water / Cooling with ice 2.1: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice 3.1: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave 4.1: pyridine / 40 °C 4.2: 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 4 steps 1.1: ammonia / toluene / 0 - 5 °C / pH 10 - 11 2.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C 3.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr 3.2: 1 h / 50 - 55 °C 4.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C 4.2: 35 - 40 °C View Scheme |
Conditions | Yield |
---|---|
In ethanol for 0.75h; | 100% |
In methanol; ethyl acetate at 20℃; for 168h; Product distribution / selectivity; | |
for 1h; |
Conditions | Yield |
---|---|
In acetone at 20℃; | 100% |
In methanol; ethyl acetate at 2 - 5℃; Product distribution / selectivity; Reflux; | |
In methanol at 20℃; for 20h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In toluene for 0.75h; | 100% |
Conditions | Yield |
---|---|
at 110 - 130℃; for 5h; | 98% |
Conditions | Yield |
---|---|
at 135℃; Neat (no solvent); | 98% |
methyl 4-hydroxylbenzoate
agomelatine
agomelatine methyl 4-hydroxybenzoate adduct
Conditions | Yield |
---|---|
at 110℃; Neat (no solvent); | 98% |
agomelatine
Conditions | Yield |
---|---|
With sulfuric acid In acetone at 10 - 20℃; Solvent; Temperature; | 96.9% |
With sulfuric acid In acetone at 10 - 20℃; Solvent; Temperature; | 13.6 g |
With sulfuric acid In ethyl acetate at 20℃; |
Conditions | Yield |
---|---|
In diethyl ether for 48h; | 96% |
at 20 - 45℃; for 480h; Sealed tube; |
Conditions | Yield |
---|---|
at 120℃; for 0.333333h; Neat (no solvent); | 96% |
In ethanol at 20℃; for 2h; Time; | 70% |
In isopropyl alcohol at 20℃; for 20h; | 41% |
agomelatine
benzenesulfonic acid
N-[2-(7-methoxyl-1-naphthyl)ethyl]acetamide benzenesulfonic acid
Conditions | Yield |
---|---|
In acetone at 25℃; Solvent; Temperature; | 95.8% |
In methanol; ethyl acetate at 2 - 20℃; Product distribution / selectivity; | |
In dichloromethane at 10 - 20℃; Solvent; Temperature; | 15.6 g |
In methanol; ethyl acetate Heating; |
toluene-4-sulfonic acid
agomelatine
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane for 0.5h; Solvent; Temperature; Reflux; | 95.8% |
agomelatine
N-[2-(7-Hydroxy-1-naphthyl)ethyl]-acetamide
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -10 - 20℃; for 2h; | 93.3% |
Stage #1: agomelatine With boron tribromide In dichloromethane at 0℃; for 2h; Stage #2: With water In dichloromethane at 0℃; | 80% |
With hydrogenchloride In water at 80℃; | 74.8% |
Conditions | Yield |
---|---|
In acetonitrile for 2h; Reflux; | 93% |
for 0.25h; |
agomelatine
N [2-(7-methoxynaphthalen-1-yl)ethyl]acetamide hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate at 10℃; Product distribution / selectivity; | 88.7% |
With hydrogenchloride In water; ethyl acetate at 10℃; for 1h; | 88.7% |
With hydrogenchloride In water; ethyl acetate at 10℃; for 1h; | 88.7% |
Conditions | Yield |
---|---|
In acetone at 0 - 10℃; | 88.2% |
In acetone at 0 - 10℃; | 1.5 g |
agomelatine
N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide In water; ethyl acetate at 20℃; for 1h; Product distribution / selectivity; | 85.3% |
With hydrogen bromide In water; ethyl acetate at 20℃; for 1h; Temperature; | 85.3% |
With hydrogen bromide In water; ethyl acetate for 1h; | 85.3% |
1. Introduction of Agomelatine
Agomelatine is one kind of off-white or white crystalline powder or white solid. The IUPAC Name of this chemical is N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide. This chemical belongs to Aromatics Compounds;Aromatics;Neurochemicals;APIS. It should be store at -20°C Freezer. Agomelatine Solubility: Soluble in Chloroform and Methanol. DMSO ≥49mg/mL Water <1mg/mL Ethanol ≥49mg/mL.
Its Classification Code is Central Nervous System Agents; Central Nervous System; Depressants; Drug / Therapeutic Agent; Hypnotics and sedatives.
2. Properties of Agomelatine
Physical properties about Agomelatine are:
(1)Melting Point: 107-109°C; (2)Boiling point: 478.8 °C at 760 mmHg; (3)Flash Point: 243.4 °C ; (4)Density: 1.109 g/cm3; (5)Surface Tension: 41.5 dyne/cm ; (6)Enthalpy of Vaporization: 74.3 kJ/mol ; (7)Vapour Pressure: 2.49E-09 mmHg at 25°C; (8)XLogP3-AA: 2.7; (9)H-Bond Donor: 1; (10)H-Bond Acceptor: 2.
3. Structure Descriptors of Agomelatine
(1)Canonical SMILES: CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC;
(2)InChI: InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17) ;
(3)InChIKey: YJYPHIXNFHFHND-UHFFFAOYSA-N.
4. Toxicity of Agomelatine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 1gm/kg (1000mg/kg) | United States Patent Document. Vol. #5318994, |
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