Product Name

  • Name

    LorcaserinA

  • EINECS 1312995-182-4
  • CAS No. 616201-80-0
  • Article Data30
  • CAS DataBase
  • Density 1.075g/cm3
  • Solubility
  • Melting Point
  • Formula C11H14Cl N
  • Boiling Point 288ºC
  • Molecular Weight 195.692
  • Flash Point 128 ºC
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 616201-80-0 (LorcaserinA)
  • Hazard Symbols
  • Synonyms (?à)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;
  • PSA 12.03000
  • LogP 2.91800

Synthetic route

1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride
953789-37-2

1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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%
N-(4-chlorophenylethyl)propyl-2-ene-1-amine hydrochloride

N-(4-chlorophenylethyl)propyl-2-ene-1-amine hydrochloride

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
N-(4-chlorophenylethyl)propyl-2-ene-1-amine trifluoroacetate

N-(4-chlorophenylethyl)propyl-2-ene-1-amine trifluoroacetate

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
1247548-14-6

N-(4-chlorophenylethyl)propyl-2-ene-1-amine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
N-allyl-N-(4-chlorophenethyl)carbamic acid tert-butyl ester

N-allyl-N-(4-chlorophenethyl)carbamic acid tert-butyl ester

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
824430-77-5

8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
34164-14-2

N-(4-chlorophenylethyl)-2-chloropropanamide

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
156-41-2

4-chlorophenylethylamine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
616202-51-8

(1R,S)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
953789-37-2

1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
6529-53-9

1-(2-bromoethyl)-4-chlorobenzene

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Reflux
2: zinc(II) chloride / 6.42 h / 125 °C
View Scheme
2-(4-Chlorophenyl)ethanol
1875-88-3

2-(4-Chlorophenyl)ethanol

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
N-(2-chloroethyl)-2-(3-chlorophenyl ) propan-1-amine

N-(2-chloroethyl)-2-(3-chlorophenyl ) propan-1-amine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
With aluminum (III) chloride at 150℃;
2-(3-chlorophenyl) propan-1-amine
1082555-06-3

2-(3-chlorophenyl) propan-1-amine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
1616729-45-3

2-(3-chlorophenyl)-N-(2,2-dimethoxyethyl)propan-1-amine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
N-(2-(3-chlorophenyl)propyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide

N-(2-(3-chlorophenyl)propyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
8-chloro-1-methyl-3-tosyl-2,3-dihydro-1H-benzo[d]azepine

8-chloro-1-methyl-3-tosyl-2,3-dihydro-1H-benzo[d]azepine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
8-chloro-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

8-chloro-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
With hydrogen bromide; propionic acid; phenol for 6h; Reflux;
(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

Allyl chloroformate
2937-50-0

Allyl chloroformate

A

allyl (S)-8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-carboxylate

allyl (S)-8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-carboxylate

B

allyl (R)-8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-carboxylate

allyl (R)-8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-carboxylate

C

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
616202-81-4

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 90℃; Reagent/catalyst; Temperature;
(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

A

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

B

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: potassium tert-butylate / dimethyl sulfoxide / 100 °C
View Scheme
(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

A

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

B

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone; water / 0 - 20 °C
2: sodium hydroxide / dimethyl sulfoxide / 100 °C
View Scheme
(S)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

(S)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

A

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

B

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 100℃; Reagent/catalyst;A n/a
B 12 %Spectr.
(S)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

(S)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

A

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone

B

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 100℃;A n/a
B 25 %Spectr.
1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene
167886-56-8

1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
4-chloro-N-(2-chloro-1-oxopropyl)benzeneacetamide

4-chloro-N-(2-chloro-1-oxopropyl)benzeneacetamide

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
1878-66-6

4-chlorophenylacetic Acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

Lorcaserin hydrochloride
846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

Conditions
ConditionsYield
With L-Tartaric acid In water; acetone at 45 - 50℃; for 0.5h;36.6%
L-Tartaric acid
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

Conditions
ConditionsYield
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
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate

Conditions
ConditionsYield
In water; acetone at 0 - 52℃; for 2.08 - 3.25h;27.1%
L-Tartaric acid
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

2C11H14ClN*C4H6O6

2C11H14ClN*C4H6O6

Conditions
ConditionsYield
In water; acetone at 0 - 55℃;24.1%
1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane
847063-13-2

1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

2-(8-chloro-1-methyl-4,5-dihydro-1H-benzazepin-3(2H)-yl)-N-(4-chlorophenethyl)propan-1-amine hydrochloride

2-(8-chloro-1-methyl-4,5-dihydro-1H-benzazepin-3(2H)-yl)-N-(4-chlorophenethyl)propan-1-amine hydrochloride

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

A

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine
616202-81-4

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine

B

lorcaserin

lorcaserin

Conditions
ConditionsYield
chiral HPLC;
L-Tartaric acid
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

Conditions
ConditionsYield
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
87-69-4

L-Tartaric acid

(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

Conditions
ConditionsYield
In water; acetone at 45℃; for 0.333333h; Product distribution / selectivity; Industry scale;
(+/-)-Lorcaserin
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine adipate salt
1361475-96-8

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine adipate salt

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine malonate salt
1361475-98-0

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine malonate salt

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glycolate
1361476-04-1

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glycolate

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine bisulfate salt
1361475-79-7

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine bisulfate salt

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemisulfate

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemisulfate

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide
1361476-15-4

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine mesylate
1361475-85-5

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine mesylate

Conditions
ConditionsYield
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
616201-80-0

(+/-)-Lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine nitrate
1361475-90-2

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine nitrate

Conditions
ConditionsYield
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

Lorcaserin A Chemical Properties

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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