4-(cyclohexanecarbonyl)-6-hydroxy-1-phenethylpiperazin-2-one
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With hydrogenchloride at 0℃; | 95% |
With sulfuric acid | 3.0 g (95%) |
With sulfuric acid In dichloromethane at 0 - 5℃; for 4h; | 170.1 g |
4-(cyclohexanecarbonyl)-6-hydroxy-1-phenethylpiperazin-2-one
B
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
In 12N-hydrochloric acid | A 95% B n/a |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 760.051 Torr; for 19h; Solvent; Inert atmosphere; | 93% |
cyclohexanylcarbonyl chloride
2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With triethylamine In 1,2-dimethoxyethane for 15h; Ambient temperature; | 90% |
With sodium carbonate In dichloromethane for 2h; Ambient temperature; | 85% |
With triethylamine In 1,2-dimethoxyethane for 20h; Ambient temperature; | 70% |
1-[2-(2-bromophenyl)ethyl]-4-(cyclohexylcarbonyl)-1,3,4-trihydropyrazin-2-one
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 16h; Heating; | 90% |
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 19 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / 2-methyltetrahydrofuran / 22 h / 80 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / methanol / 19 h / 20 °C / 760.05 Torr / Inert atmosphere View Scheme |
N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide
chloroacetyl chloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20 - 25℃; for 0.7h; | 88% |
Stage #1: N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide; chloroacetyl chloride With sodium hydroxide In dichloromethane for 0.5h; Stage #2: With N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 2h; Reflux; | 81% |
Stage #1: N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide; chloroacetyl chloride With sodium hydroxide In dichloromethane at 20℃; for 0.5h; Stage #2: With benzyltrimethylammonium chloride In dichloromethane for 2h; Reflux; | 78% |
Stage #1: N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclohexanecarboxylic acid amide; chloroacetyl chloride With sodium hydroxide In dichloromethane at 0℃; for 0.5h; Stage #2: With tetrabutylammomium bromide In dichloromethane for 3h; Reflux; | 68% |
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water Inert atmosphere; | 56% |
cyclohexanylcarbonyl chloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: C14H22N2O3*0.5H2O4S at 35 - 45℃; for 10h; Stage #2: cyclohexanylcarbonyl chloride With lithium hydroxide In water at 5℃; for 5h; | 86.5% |
1-Cyclohexylcarbonylaminomethyl-2-chloracetyl-1,2,3,4-tetrahydro-isochinolin
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 80℃; for 0.7h; | 86% |
cyclohexanylcarbonyl chloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: C14H22N2O3*H3O4P With phosphoric acid at 10 - 20℃; for 12h; Stage #2: cyclohexanylcarbonyl chloride With calcium bicarbonate In water at 0℃; for 5h; | 86% |
cyclohexanylcarbonyl chloride
N-2-phenylethyl 2-N-(2,2-dimethoxyethylamino)acetamide hydrochloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: N-2-phenylethyl 2-N-(2,2-dimethoxyethylamino)acetamide hydrochloride With sulfuric acid In dichloromethane at 5 - 20℃; for 3.5h; Cooling with ice; Industrial scale; Stage #2: cyclohexanylcarbonyl chloride With sodium carbonate at 5 - 20℃; for 2.5h; Reagent/catalyst; Solvent; Temperature; Industrial scale; | 85.1% |
N-(2,2-dimethoxyethyl)-N-(2-oxo-2-(2-phenethylamino)-ethyl)cyclohexanecarboxamide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With methanesulfonic acid In 1,2-dichloro-ethane for 6h; Heating; | 85% |
Stage #1: N-(2,2-dimethoxyethyl)-N-(2-oxo-2-(2-phenethylamino)-ethyl)cyclohexanecarboxamide With methanesulfonic acid at 0 - 70℃; for 6h; Pictet-Spengler cyclisation; Stage #2: With water; sodium hydroxide pH=8; Pictet-Spengler cyclisation; Cooling with ice; | 65% |
Multi-step reaction with 2 steps 1: 95 percent / methanesulfonic acid / CH2Cl2 / 3 h / Ambient temperature 2: conc. H2SO4 / 3 h / Ambient temperature View Scheme |
cyclohexanylcarbonyl chloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: C14H22N2O3*H2O4S With sulfuric acid at 0 - 5℃; for 10h; Stage #2: cyclohexanylcarbonyl chloride With sodium carbonate In water at 0℃; for 4.5h; | 85% |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 10h; Reagent/catalyst; Solvent; Temperature; Cooling with ice; | 76.8% |
N-(2,2-diethoxy)ethyl-N-2-phenylethyl 2-N-cyclohexylcarbonylaminoacetamide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With methanesulfonic acid In dichloromethane for 48h; Heating; | 73% |
Multi-step reaction with 2 steps 1: 91 percent / methanesulfonic acid / CH2Cl2 / 3 h / Ambient temperature 2: conc. H2SO4 / 3 h / Ambient temperature View Scheme |
cyclohexanylcarbonyl chloride
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: C14H22N2O3*(x)ClH at 10 - 15℃; for 8h; Stage #2: cyclohexanylcarbonyl chloride With calcium hydroxide In water at 10℃; for 4h; | 70.9% |
4-(cyclohexylcarbonyl)-3,4-dihydro-1-(2-phenylethyl)-2(1H)-pyrazinone
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 3h; | 70% |
With sulfuric acid for 3h; Ambient temperature; Yield given; |
cyclohexanecarboxylic acid {[(2-ethoxy-2-(polystyryl)oxy-ethyl)-phenethyl-carbamoyl]-methyl}-amide, via coupling with (cyclohexanecarbonyl-amino)-acetic acid
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With methanesulfonic acid In nitromethane at 60℃; for 16h; | 57% |
Cyclohexanecarboxylic acid bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl-[(methoxymethyl-carbamoyl)-methyl]-amide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
at 400 - 425℃; for 8h; | 49% |
N-(2-phenylethyl)-N-(cyanomethyl)amide of cyclohexylcarbonylglycine
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With formic acid; sulfuric acid; nickel 1.) water, reflux, 1 h, 2.) 20 deg C, 3 h; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: 53 percent / formic acid, Raney Ni / H2O / 1 h / Heating 2: 70 percent / conc. H2SO4 / 3 h / 20 °C View Scheme |
(cyclohexanecarbonyl-amino)-acetic acid
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 2: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 3: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 1.) dicyclohexylcarbodiimide / 1.) CHCl3, 20 deg C, 30 min, 2.) CHCl3, 20 deg C, 76 h 2: 53 percent / formic acid, Raney Ni / H2O / 1 h / Heating 3: 70 percent / conc. H2SO4 / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) dicyclohexylcarbodiimide / 1.) CHCl3, 20 deg C, 30 min, 2.) CHCl3, 20 deg C, 76 h 2: 1.) Raney Ni, formic acid, 2.) conc. H2SO4 / 1.) water, reflux, 1 h, 2.) 20 deg C, 3 h View Scheme |
2-(2-bromophenyl)ethanamine
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 40 percent / NaBH(OAc)3 / 1,2-dichloro-ethane; various solvent(s) / 3 h / 20 °C 2: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 3: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 4: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 68 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt; DMAP / CH2Cl2 / 16 h / 20 °C 2: 60 percent / tin(II) trifluoromethanesulfonate / acetone / 40 °C 3: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
phenylmethyl 2-(cyclohexylcarbonylamino)acetate
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / H2 / Pd/C / aq. ethanol / 1.5 h 2: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 3: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 4: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
(2,2-dimethoxyethyl)-[2-(2-bromophenyl)ethyl]amine
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 2: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 3: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
2-[N-(2,2-dimethoxyethyl)cyclohexylcarbonylamino]acetic acid
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt; DMAP / CH2Cl2 / 16 h / 20 °C 2: 60 percent / tin(II) trifluoromethanesulfonate / acetone / 40 °C 3: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
phenylmethyl 2-[N-(2,2-dimethoxyethyl)cyclohexylcarbonylamino]acetate
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / H2 / Pd/C / aq. ethanol 2: 68 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt; DMAP / CH2Cl2 / 16 h / 20 °C 3: 60 percent / tin(II) trifluoromethanesulfonate / acetone / 40 °C 4: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
N-(2,2-dimethoxyethyl)-N-(2-oxo-2-(2-(2-bromophenyl)ethylamino)ethyl)cyclohexanecarboxamide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / tin(II) trifluoromethanesulfonate / acetone / 40 °C 2: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
N-(2,2-dimethoxyethyl)-N-[2-(2-bromophenyl)ethyl]-2-(cyclohexylcarbonylamino)acetamide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 2: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
Cyclohexanecarboxylic acid
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 61 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C 2: 98 percent / H2 / Pd/C / aq. ethanol / 1.5 h 3: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 4: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 5: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 61 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C 2: 98 percent / H2 / Pd/C / aq. ethanol / 1.5 h 3: 88 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 48 h / 20 °C 4: 76 percent / tin(II) trifluoromethanesulfonate / acetone / 48 h / 40 °C 5: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 82 percent / PyBroP; 1-hydroxy-7-azabenzotriazole; DIPEA / CH2Cl2 / 16 h / 20 °C 2: 98 percent / H2 / Pd/C / aq. ethanol 3: 68 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOBt; DMAP / CH2Cl2 / 16 h / 20 °C 4: 60 percent / tin(II) trifluoromethanesulfonate / acetone / 40 °C 5: 90 percent / AIBN; Bu3SnH / toluene / 16 h / Heating View Scheme |
N-(2-phenylethyl)aminoacetaldehyde diethyl acetal
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NEt3 / 1.) CH2Cl2, 0 deg C, 1 h; 2.) CH2Cl2, reflux, 7 h 2: 91 percent / methanesulfonic acid / CH2Cl2 / 3 h / Ambient temperature 3: conc. H2SO4 / 3 h / Ambient temperature View Scheme |
N,N-dimethyl-formamide
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 1h; Stage #2: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one at 60℃; for 5h; Vilsmeier formylation; Stage #3: With perchloric acid In methanol | 95% |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
Conditions | Yield |
---|---|
With hydrogenchloride In water Reflux; | 91.2% |
With hydrogenchloride In ethanol for 60h; Reflux; | 83% |
Stage #1: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one With hydrogenchloride; water for 24h; Reflux; Stage #2: With sodium hydroxide In water regioselective reaction; | 80% |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 168h; Ambient temperature; | 81% |
Multi-step reaction with 2 steps 1: 38 percent / sulfur / 2 h / 180 °C 2: 73 percent / 85percent MCPBA / CH2Cl2 View Scheme |
4-methoxy-benzaldehyde
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-(cyclohexylcarbonyl)-3-(4-methoxybenzylidene)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; Claisen-Schmidt Condensation; Reflux; | 75% |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With Lawessons reagent In toluene for 3h; Heating; | 70% |
thiophene-2-carbaldehyde
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-(cyclohexylcarbonyl)-3-(thiophen-2-methylene)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; Claisen-Schmidt Condensation; Reflux; | 70% |
4-methylpiperidin
formaldehyd
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-(cyclohexylcarbonyl)-3-((4-methylpiperidin-1-yl)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: 4-methylpiperidin; formaldehyd In ethanol for 0.5h; Mannich Aminomethylation; Reflux; Stage #2: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one In ethanol for 8h; Reflux; | 65% |
1-methyl-piperazine
formaldehyd
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-2-(cyclohexylcarbonyl)-3-((4-methylpiperazin-1-yl)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: 1-methyl-piperazine; formaldehyd In ethanol for 0.5h; Mannich Aminomethylation; Reflux; Stage #2: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one In ethanol for 8h; Reflux; | 60% |
formaldehyd
di-n-propylamine
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-(cyclohexylcarbonyl)-3-dipropylaminomethyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: formaldehyd; di-n-propylamine In ethanol for 0.5h; Mannich Aminomethylation; Reflux; Stage #2: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one In ethanol for 8h; Reflux; | 60% |
formaldehyd
ethanolamine
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-2-(cyclohexylcarbonyl)-3-((2-hydroxyethylamino)methyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
Stage #1: formaldehyd; ethanolamine In ethanol for 0.5h; Mannich Aminomethylation; Reflux; Stage #2: 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one In ethanol for 8h; Reflux; | 60% |
benzaldehyde
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
2-(cyclohexylcarbonyl)-3-benzylidene-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; Claisen-Schmidt Condensation; Reflux; | 60% |
2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one
Conditions | Yield |
---|---|
With Lawessons reagent In toluene for 3h; Heating; | 50% |
Molecular Structure:
Molecular Formula: C19H24N2O2
Molecular Weight: 312.4061
IUPAC Name: 2-(Cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one
Synonyms of Biltricide (CAS NO.55268-74-1): Drontal ; Drontal Plus ; Vercom ; 2-(Cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino(2,1-a)isoquinolin-4-one ; 4H-Pyrazino(2,1-a)isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro- ; 5-24-03-00361 (Beilstein Handbook Reference) ; BRN 0761557 ; CCRIS 4114 ; Cutter Tape Tabs ; Droncit ; EINECS 259-559-6 ; Embay 8440 ; Praziquantel ; Praziquantelum ; Praziquantelum [INN-Latin] ; Pyquiton ; UNII-6490C9U457
CAS NO: 55268-74-1
Classification Code: Anthelmintic [veterinary] ; Anthelmintics ; Anti-Infective Agents ; Antiparasitic Agents ; Drug / Therapeutic Agent ; Mutation data
Melting point: 136-138 °C
Index of Refraction: 1.615
Molar Refractivity: 88.76 cm3
Molar Volume: 254.2 cm3
Surface Tension: 55.2 dyne/cm
Density: 1.22 g/cm3
Flash Point: 254.6 °C
Enthalpy of Vaporization: 82.27 kJ/mol
Boiling Point: 544.1 °C at 760 mmHg
Vapour Pressure: 6.71E-12 mmHg at 25°C
Laboratories developed the Biltricide for parasitological research of Bayer AG in Germany (Elberfeld) in the mid 1970s. The World Health Organization includes it on its Model List of Essential Medicines.
1. Biltricide (CAS NO.55268-74-1) is used to treat Echinococcosis
2.It is used to Cysticercosis (though it has been judged less effective than albendazole in treatment of neurocysticercosis.)
3.It is used to Intestinal tapeworms. In veterinary medicine it is widely used against tapeworms, either alone under the trade name Droncit, or in combination with pyrantel pamoate under the trade name Drontal.
4.It is used against Schistosoma.As of 2005, Biltricide is the primary treatment for human schistosomiasis, for which it is usually effective in a single dose.
5.It is used to treat liver flukes (such as Clonorchis sinensis) except for fascioliasis.
6.It is also used to treat paragonimiasis.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 200mg/kg (200mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
mouse | LD50 | intramuscular | > 2gm/kg (2000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
mouse | LD50 | intraperitoneal | 376mg/kg (376mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 228, 1989. | |
mouse | LD50 | oral | 2454mg/kg (2454mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
mouse | LD50 | subcutaneous | 7172mg/kg (7172mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
rabbit | LD50 | oral | 1050mg/kg (1050mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
rat | LD50 | intramuscular | > 2gm/kg (2000mg/kg) | Drugs in Japan Vol. -, Pg. 965, 1990. | |
rat | LD50 | intraperitoneal | 586mg/kg (586mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 228, 1989. | |
rat | LD50 | oral | 2840mg/kg (2840mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. | |
rat | LD50 | subcutaneous | > 16gm/kg (16000mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981. |
EPA Genetic Toxicology Program.
Hazard Codes of Biltricide (CAS NO.55268-74-1): F,C
Risk Statements: 11-34
R11: Highly flammable.
R34: Causes burns.
Safety Statements: 16-26-36/37/39-45
S16: Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 1
RTECS: UQ4150000
Poison by intraperitoneal route. Moderately toxic by ingestion and other routes. Human mutation data reported. When Biltricide was heated to decomposition, it emits toxic fumes of NOx.
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