1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-benzene at 120 - 125℃; Inert atmosphere; | 99% |
With aluminum (III) chloride at 120 - 125℃; for 3h; Inert atmosphere; Large scale; | 97% |
With aluminum (III) chloride In 1,2-dichloro-benzene at 135 - 140℃; | 96.1% |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-benzene at 110℃; for 4h; Solvent; Temperature; Reagent/catalyst; Friedel-Crafts Alkylation; Inert atmosphere; Large scale; | 92.3% |
With aluminum (III) chloride In 1,2-dichloro-benzene at 110℃; Friedel-Crafts Alkylation; | 84.5% |
With aluminum (III) chloride In 1,2-dichloro-benzene at 110℃; | 84.5% |
With zinc(II) chloride at 125℃; for 6.41667h; Reagent/catalyst; Friedel-Crafts Alkylation; | 230 mg |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-benzene at 110℃; Friedel-Crafts Alkylation; | 83.9% |
With aluminum (III) chloride In 1,2-dichloro-benzene at 110℃; | 83.9% |
N-(4-chlorophenylethyl)propyl-2-ene-1-amine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride In 1,2-dichloro-benzene at 90℃; Friedel-Crafts Alkylation; | 82.1% |
With aluminum (III) chloride at 125℃; for 6.41667h; Friedel-Crafts Alkylation; | 230 mg |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride In chlorobenzene at 110℃; Solvent; Temperature; | 81.6% |
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate / 20 °C / pH 2 / Large scale 2: aluminum (III) chloride / 1,2-dichloro-benzene / 4 h / 110 °C / Inert atmosphere; Large scale View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate / 20 °C 2: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C View Scheme | |
Multi-step reaction with 2 steps 1: dichloromethane / 25 °C 2: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / water; ethyl acetate / 20 °C 2: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C View Scheme |
8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With borane-THF at 20℃; for 10h; | 70% |
With borane In diethyl ether | |
With sodium tetrahydroborate; chloro-trimethyl-silane In 1,2-dichloro-ethane at 70℃; for 20h; Solvent; Temperature; Cooling with ice; | 0.89 g |
N-(4-chlorophenylethyl)-2-chloropropanamide
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlCl3 / 150 - 200 °C 2: BH3 / diethyl ether View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 8 h / 150 °C 2: chloro-trimethyl-silane; sodium tetrahydroborate / 1,2-dichloro-ethane / 20 h / 70 °C / Cooling with ice View Scheme |
4-chlorophenylethylamine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 2: AlCl3 / 150 - 200 °C 3: BH3 / diethyl ether View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 18 h / 20 °C 2: zinc(II) chloride / 6.42 h / 125 °C View Scheme | |
Multi-step reaction with 4 steps 1: dmap / dichloromethane / 0 - 20 °C / Large scale 2: potassium carbonate; potassium hydroxide; tetrabutylammomium bromide / toluene / 5 h / 80 °C / Large scale 3: hydrogenchloride / ethyl acetate / 20 °C / pH 2 / Large scale 4: aluminum (III) chloride / 1,2-dichloro-benzene / 4 h / 110 °C / Inert atmosphere; Large scale View Scheme |
(1R,S)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 60℃; for 3.5h; | 35 mg |
With sodium hydroxide In methanol | |
With sodium hydroxide In methanol; water at 60℃; for 3.5h; |
1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride
1,2-dichloro-benzene
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Stage #1: 1-[[2-(4-chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride; 1,2-dichloro-benzene With aluminum (III) chloride at 126℃; for 16h; Friedel Crafts; Industry scale; Inert atmosphere; Stage #2: With sodium hydroxide In cyclohexane; water pH=12; Product distribution / selectivity; Industry scale; |
1-(2-bromoethyl)-4-chlorobenzene
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Reflux 2: zinc(II) chloride / 6.42 h / 125 °C View Scheme |
2-(4-Chlorophenyl)ethanol
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; dmap / dichloromethane / 4 h 2.1: dichloromethane / Reflux 2.2: Reflux 3.1: zinc(II) chloride / 6.42 h / 125 °C View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With aluminum (III) chloride at 150℃; |
2-(3-chlorophenyl) propan-1-amine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 120 °C / Inert atmosphere 2: pyridine / dichloromethane / 2.5 h / 20 °C 3: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 4: hydrogen; platinum(IV) oxide; hydrogenchloride / methanol / 48 h / 25 °C / 3750.38 Torr 5: hydrogen bromide; phenol; propionic acid / 6 h / Reflux View Scheme |
2-(3-chlorophenyl)-N-(2,2-dimethoxyethyl)propan-1-amine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / 2.5 h / 20 °C 2: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 3: hydrogen; platinum(IV) oxide; hydrogenchloride / methanol / 48 h / 25 °C / 3750.38 Torr 4: hydrogen bromide; phenol; propionic acid / 6 h / Reflux View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 2: hydrogen; platinum(IV) oxide; hydrogenchloride / methanol / 48 h / 25 °C / 3750.38 Torr 3: hydrogen bromide; phenol; propionic acid / 6 h / Reflux View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; platinum(IV) oxide; hydrogenchloride / methanol / 48 h / 25 °C / 3750.38 Torr 2: hydrogen bromide; phenol; propionic acid / 6 h / Reflux View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With hydrogen bromide; propionic acid; phenol for 6h; Reflux; |
Allyl chloroformate
C
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Stage #1: (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride; Allyl chloroformate With triethylamine In dichloromethane at 0 - 20℃; Stage #2: With potassium tert-butylate In dimethyl sulfoxide at 100℃; | A n/a B n/a C 28 %Spectr. |
(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 90℃; Reagent/catalyst; Temperature; |
B
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: potassium tert-butylate / dimethyl sulfoxide / 100 °C View Scheme |
B
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetone; water / 0 - 20 °C 2: sodium hydroxide / dimethyl sulfoxide / 100 °C View Scheme |
B
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 100℃; Reagent/catalyst; | A n/a B 12 %Spectr. |
B
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 100℃; | A n/a B 25 %Spectr. |
1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; potassium hydroxide; tetrabutylammomium bromide / toluene / 5 h / 80 °C / Large scale 2: hydrogenchloride / ethyl acetate / 20 °C / pH 2 / Large scale 3: aluminum (III) chloride / 1,2-dichloro-benzene / 4 h / 110 °C / Inert atmosphere; Large scale View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate; potassium hydroxide; tetrabutylammomium bromide / toluene / 80 °C 2: dichloromethane / 25 °C 3: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate; potassium hydroxide; tetrabutylammomium bromide / toluene / 80 °C 2: hydrogenchloride / ethyl acetate / 20 °C 3: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; aluminum (III) chloride; chloro-trimethyl-silane / tetrahydrofuran / 24 h / 70 °C / Inert atmosphere 2: aluminum (III) chloride / 1,2-dichloro-benzene / 16 h / 130 °C View Scheme |
4-chlorophenylacetic Acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: boric acid / toluene / 24 h / 40 - 135 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 2.75 h / 8 - 45 °C 3: aluminum (III) chloride / 1,2-dichloro-benzene / 8 h / 5 - 125 °C View Scheme |
(+/-)-Lorcaserin
Lorcaserin hydrochloride
Conditions | Yield |
---|---|
Stage #1: (+/-)-Lorcaserin With L-Tartaric acid In ethanol; water at 80℃; Stage #2: With potassium carbonate In water pH=12; Stage #3: With hydrogenchloride In water; ethyl acetate at 5 - 10℃; for 1h; | 80% |
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: hydrogenchloride / ethyl acetate; water / pH 5 / Industry scale View Scheme | |
Multi-step reaction with 2 steps 1.1: water; tert-butyl alcohol / 10 h / 20 °C 2.1: sodium hydroxide / water / 0.17 h / 20 °C 2.2: 0.08 h / 20 °C View Scheme |
L-Tartaric acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
In water; tert-butyl alcohol at 20 - 78℃; for 4h; | 48% |
In water; acetone at 58℃; for 2h; Concentration; | 37.1% |
In acetone at 50℃; for 3h; | 33.2% |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
With L-Tartaric acid In water; acetone at 45 - 50℃; for 0.5h; | 36.6% |
L-Tartaric acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
In water; acetone at 50℃; for 3h; Large scale; | 33.2% |
Stage #1: L-Tartaric acid; (+/-)-Lorcaserin In water; acetone at 50℃; for 3h; Stage #2: In water; acetone at 0 - 5℃; for 5h; Reflux; | 32.8% |
In water; acetone at 45 - 50℃; for 3h; | 17.9% |
In water; acetone at 47 - 52℃; for 0.0833333 - 0.25h; L-(+)-tartaric acid salt of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; Resolution of racemate; | n/a |
L-Tartaric acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
In water; acetone at 0 - 52℃; for 2.08 - 3.25h; | 27.1% |
Conditions | Yield |
---|---|
In water; acetone at 0 - 55℃; | 24.1% |
1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Stage #1: 1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane; (+/-)-Lorcaserin With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70 - 75℃; for 5h; Stage #2: With isopropyl alcohol hydrogen chloride at 0 - 5℃; for 1h; | 18.3% |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Stage #1: (+/-)-Lorcaserin With L-Tartaric acid In water; acetone at 45 - 50℃; for 3h; Stage #2: With ammonium hydroxide In water; ethyl acetate for 0.5h; pH=> 10; Further stages; | 17.9% |
(+/-)-Lorcaserin
A
(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine
Conditions | Yield |
---|---|
chiral HPLC; |
L-Tartaric acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
In water; acetone at 47 - 52℃; for 2 - 3h; | n/a |
In water; acetone at 45℃; for 0.333333h; Temperature; Large scale; | 158 kg |
L-Tartaric acid
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
In water; acetone at 45℃; for 0.333333h; Product distribution / selectivity; Industry scale; |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine adipate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: acetone / 0.08 h / 62 °C View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine malonate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: Isopropyl acetate View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glycolate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: 60 °C / Cooling View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine bisulfate salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: sulfuric acid View Scheme |
(+/-)-Lorcaserin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: sulfuric acid View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: hydrogen bromide / water / 38 °C / Inert atmosphere View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine mesylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: 20 - 60 °C View Scheme |
(+/-)-Lorcaserin
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine nitrate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; acetone / 0.33 h / 45 °C / Industry scale 2: potassium carbonate / ethyl acetate; water / 15 - 22 °C / Industry scale 3: nitric acid / water View Scheme |
Product Name: LorcaserinA
Synonyms of LorcaserinA (CAS NO.616201-80-0): 8-Chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine
CAS NO: 616201-80-0
Molecular Formula of LorcaserinA (CAS NO.616201-80-0): C11H14ClN
Molecular Weight: 195.69
Molecular Structure:
Boiling Point: 288 º C
Density of LorcaserinA (CAS NO.616201-80-0): 1.075g/cm3
Flash Point: 128 º C
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