616201-80-0

Basic information

• Product Name: LorcaserinA
• Synonyms: LorcaserinA;8-Chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine;1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-Methyl-;8-Chloro-1-Methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;7-chloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
• CAS NO: 616201-80-0
• Molecular Formula: C₁₁H₁₄ClN
• Molecular Weight: 195.69
• EINECS: 1312995-182-4
• Mol File: 616201-80-0.mol

Chemical Properties

• Boiling Point: 288 ºC
• Flash Point: 128 ºC
• Appearance: /
• Density: 1.075
• PKA: 9.99±0.40(Predicted)
• CAS DataBase Reference: LorcaserinA(CAS DataBase Reference)
• NIST Chemistry Reference: LorcaserinA(616201-80-0)
• EPA Substance Registry System: LorcaserinA(616201-80-0)

Safety Data

• Hazardous Substances Data: 616201-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
LorcaserinA is used as an appetite suppressant for the treatment of obesity. It helps individuals lose weight by promoting a feeling of fullness, which encourages the consumption of smaller meal portions and aids in resisting food cravings.
Used in Weight Management Programs:
LorcaserinA is used as a weight loss aid in conjunction with a healthy diet and exercise regimen. Studies have demonstrated that its use can lead to significant weight loss, making it a valuable component of comprehensive weight management programs.
However, it is important to note that LorcaserinA comes with potential side effects such as headache, dizziness, and nausea. Additionally, it is not recommended for use in individuals with congestive heart failure, valvular heart disease, or uncontrolled hypertension. Due to these considerations, LorcaserinA should be used under the guidance of a healthcare professional to ensure safe and effective weight loss.

Synthetic route

1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride (953789-37-2) → (+/-)-Lorcaserin (616201-80-0)

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%

N-(4-chlorophenylethyl)propyl-2-ene-1-amine hydrochloride → (+/-)-Lorcaserin (616201-80-0)

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

N-(4-chlorophenylethyl)propyl-2-ene-1-amine trifluoroacetate → (+/-)-Lorcaserin (616201-80-0)

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 (1247548-14-6) → (+/-)-Lorcaserin (616201-80-0)

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

N-allyl-N-(4-chlorophenethyl)carbamic acid tert-butyl ester → (+/-)-Lorcaserin (616201-80-0)

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 (824430-77-5) → (+/-)-Lorcaserin (616201-80-0)

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 (34164-14-2) → (+/-)-Lorcaserin (616201-80-0)

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 (156-41-2) → (+/-)-Lorcaserin (616201-80-0)

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 (616202-51-8) → (+/-)-Lorcaserin (616201-80-0)

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 (953789-37-2) + 1,2-dichloro-benzene (95-50-1) → (+/-)-Lorcaserin (616201-80-0)

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 (6529-53-9) → (+/-)-Lorcaserin (616201-80-0)

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 (1875-88-3) → (+/-)-Lorcaserin (616201-80-0)

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

N-(2-chloroethyl)-2-(3-chlorophenyl ) propan-1-amine → (+/-)-Lorcaserin (616201-80-0)

Conditions	Yield
With aluminum (III) chloride at 150℃;

2-(3-chlorophenyl) propan-1-amine (1082555-06-3) → (+/-)-Lorcaserin (616201-80-0)

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 (1616729-45-3) → (+/-)-Lorcaserin (616201-80-0)

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

N-(2-(3-chlorophenyl)propyl)-N-(2,2-dimethoxyethyl)-4-methylbenzenesulfonamide → (+/-)-Lorcaserin (616201-80-0)

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

8-chloro-1-methyl-3-tosyl-2,3-dihydro-1H-benzo[d]azepine → (+/-)-Lorcaserin (616201-80-0)

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

8-chloro-1-methyl-3-tosyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine → (+/-)-Lorcaserin (616201-80-0)

Conditions	Yield
With hydrogen bromide; propionic acid; phenol for 6h; Reflux;

(S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride + Allyl chloroformate (2937-50-0) → allyl (S)-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 + (+/-)-Lorcaserin (616201-80-0)

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 (616202-81-4) → (+/-)-Lorcaserin (616201-80-0)

Conditions	Yield
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 → 1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone + (+/-)-Lorcaserin (616201-80-0)

Conditions	Yield
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 → 1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone + (+/-)-Lorcaserin (616201-80-0)

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

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

Conditions	Yield
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 → 1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-yl)-2-phenylethanone + (+/-)-Lorcaserin (616201-80-0)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 100℃;	A n/a B 25 %Spectr.

1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene (167886-56-8) → (+/-)-Lorcaserin (616201-80-0)

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

4-chloro-N-(2-chloro-1-oxopropyl)benzeneacetamide → (+/-)-Lorcaserin (616201-80-0)

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 (1878-66-6) → (+/-)-Lorcaserin (616201-80-0)

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 (616201-80-0) → Lorcaserin hydrochloride (846589-98-8)

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 (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate

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 (616201-80-0) → bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

Conditions	Yield
With L-Tartaric acid In water; acetone at 45 - 50℃; for 0.5h;	36.6%

L-Tartaric acid (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

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 (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate

Conditions	Yield
In water; acetone at 0 - 52℃; for 2.08 - 3.25h;	27.1%

L-Tartaric acid (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → 2C11H14ClN*C4H6O6

Conditions	Yield
In water; acetone at 0 - 55℃;	24.1%

1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane (847063-13-2) + (+/-)-Lorcaserin (616201-80-0) → 2-(8-chloro-1-methyl-4,5-dihydro-1H-benzazepin-3(2H)-yl)-N-(4-chlorophenethyl)propan-1-amine hydrochloride

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 (616201-80-0) → (S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

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 (616201-80-0) → (S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine (616202-81-4) + lorcaserin

Conditions	Yield
chiral HPLC;

L-Tartaric acid (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

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 (87-69-4) + (+/-)-Lorcaserin (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

Conditions	Yield
In water; acetone at 45℃; for 0.333333h; Product distribution / selectivity; Industry scale;

(+/-)-Lorcaserin (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine adipate salt (1361475-96-8)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine malonate salt (1361475-98-0)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glycolate (1361476-04-1)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine bisulfate salt (1361475-79-7)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemisulfate

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (1361476-15-4)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine mesylate (1361475-85-5)

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 (616201-80-0) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine nitrate (1361475-90-2)

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

Upstream product

• 953789-37-2 1-[[2-(4-chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride 
• 95-50-1 1,2-dichloro-benzene 
• 1247548-14-6 N-(4-chlorophenylethyl)propyl-2-ene-1-amine 
• 6529-53-9 1-(2-bromoethyl)-4-chlorobenzene 
• 1875-88-3 2-(4-Chlorophenyl)ethanol 
• 1878-66-6 4-chlorophenylacetic Acid 
• 1030624-36-2 2-(4-chlorophenyl)-N-(2-hydroxypropyl)acetamide 
• 847063-13-2 1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane 
• 937-20-2 p-chlorophenacyl chloride 
• 140-53-4 p-chlorobenzyl cyanide 
• 167886-56-8 1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene 
• 1006037-59-7 (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride 
• 616202-81-4 (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 2937-50-0 Allyl chloroformate 

Downstream Products

• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate 
• 824430-78-6 bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate 
• 824430-78-6 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate 
• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate 
• 846589-98-8 Lorcaserin hydrochloride 
• 616202-92-7 lorcaserin 
• 1431697-94-7 (±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 824430-78-6 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate 
• 824430-78-6 2C₁₁H₁₄ClN*C₄H₆O₆ 
• 1006037-59-7 (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride 
• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate 
• 616202-81-4 (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 

Relevant articles and documents

Niclosin hydrochloride pellet, and preparation method and preparation thereof

A lorcaserin hydrochloride mini-pill is provided. The mini-pill comprises a blank pill core, a medicine loading layer, a slow-release layer and a quick-release layer in order from inside to outside. The medicine loading layer comprises lorcaserin hydrochloride, lactose monohydrate, highly substituted hydroxypropylcellulose and talcum powder. The slow-release layer comprises ethyl cellulose, highly substituted hydroxypropylcellulose, talcum powder and triethyl citrate. The quick-release layer comprises lorcaserin hydrochloride, lactose monohydrate, highly substituted hydroxypropylcellulose and talcum powder. The mass ratio of the sum of the weight of the blank pill core and the weight of the medicine loading layer to the mass of the slow-release layer is 1:(0.25-0.35). The mini-pill comprises the slow-release layer and the quick-release layer, and therefore a medicine can rapidly work and functions of the medicine in a body are prolonged. A preparing method of the lorcaserin hydrochloride mini-pill and a preparation of the lorcaserin hydrochloride mini-pill are also provided.

Method for preparing lorcaserin

The invention discloses a method for preparing lorcaserin. Specifically, the method comprises the steps: taking p-chlorophenylacetonitrile as an initial raw material, preparing p-chlorophenylethylamine through reduction; carrying out a reaction with p-toluenesulfonyl chloride to form an amino occupying intermediate; enabling the intermediate to carry out a reaction with monochloroacetone under analkaline condition to form N-(2-(4-chlorphenyl)ethyl)-4-methyl-N-(2-propionyl)benzenesulfonamide, and then carrying out reduction, chlorination, p-toluenesulfonyl removal and intramolecular Friedel-Crafts alkylation to synthesize 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzoazepine, carrying out L-(+)-tartaric acid resolution and alkalization on azepine to remove tartaric acid, and acting with hydrogen chloride diethyl ether to salify to prepare lorcaserin. The method has the characteristics of simple synthesis method, good reaction selectivity, high product purity, environmental protectionand low preparation cost.

Preparation method of key intermediate I of lorcaserin

The invention discloses a preparation method of a key intermediate I of lorcaserin. The preparation method comprises the steps as follows: (1) in an organic solvent A, 2,4'-dichloroacetophenone is subjected to a condensation reaction with isopropanolamine under catalysis of alkali, and 1-(4-chlorophenyl)-2-((2-hydroxypropyl)amino)ethane-1-one is obtained; (2) the 1-(4-chlorophenyl)-2-((2-hydroxypropyl)amino)ethane-1-one obtained in the step (1) is subjected to catalytic reduction with sodium borohydride and acid in a solvent B, and the key intermediate I of lorcaserin is obtained. The preparation method can synthesize the key intermediate I of lorcaserin from cheap and easily available raw materials under mild reaction conditions, has the advantages of being simple to operate, low in costand high in yield, and is energy-saving, environmentally friendly and suitable for mass production.

Preparation method of lorcaserin intermediate

The invention discloses a preparation method of a lorcaserin intermediate (I). According to the preparation method, p-chlorobenzyl cyanide is taken as the primary raw material, and the lorcaserin intermediate (I) is obtained after reduction reactions and condensation reactions. The primary raw materials (p-chlorobenzyl cyanide and 1-chloro-2-propanol) are cheap and easily available; raw materials, which can easily get polluted and are explosive, such as sulfoxide chloride, hydrobromic acid, borane, and the like are not used; the preparation method will not produce a large amount of wastewater and is beneficial for the environment protection; moreover, the requirements on the protection of workers are lowered, and safe production is guaranteed. The route design is novel, the raw materials are easily available, the operation is simple and feasible, and the preparation method is environment-friendly and can be applied to massive industrial production.

Preparation method and use of lorcaserin hydrochloride

The invention provides a preparation method of lorcaserin hydrochloride, wherein the preparation method comprises the synthetic route described in the specification. The preparation method of lorcaserin hydrochloride has the advantages of simpliness, cheap and easily available raw materials, convenient and safe post-processing, and more green and environmental-protection preparation process, and is an economic synthetic method which can be industrialized.

Preparation method for hemihydrate lorcaserin hydrochloride

The invention discloses a preparation method for hemihydrate lorcaserin hydrochloride. The preparation method comprises the following steps: (1) making a compound shown as a formula III react with ammonia to obtain a compound shown as a formula II; (2) under the protection of nitrogen gas, dissolving the compound shown as the formula II in an organic solvent, adding a hydrogen chloride solution of which the solvent is the organic solvent to salify, and adding water and cyclohexane to form a hemihydrate in order to obtain the compound shown as a formula I, wherein the organic solvent is isopropanol or 1,4-dioxane. In the preparation method disclosed by the invention, ammonium hydroxide substitutes for potassium carbonate in the prior art, so that unqualified ignition residues of a finial product caused by potassium chloride generated after salt removal can be avoided; an isopropoxide hydrochloride solution substitutes for the conventional hydrogen chloride gas, so that other impurities can be prevented from being introduced in a preparation process under the improper control of dosage and rate of the gas.

A preparing method of (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, a lorcaserin intermediate

A preparing method of (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is a lorcaserin intermediate is disclosed. The method includes (1) dehydrating a compound 1 and a compound 2 under catalysis by boric acid to generate an amide 3, (2) reducing the intermediate 3 with a borane dimethylsulfide complex to obtain a compound 4, and (3) subjecting the compound 4 to direct ring closing with the existence of aluminum chloride to generate the lorcaserin intermediate that is the (R,S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine that is the compound 6. The method avoids use of 3,4,5-trimethoxyphenylboronic acid that is an expensive reagent, thus reducing the cost. The method avoids use of thionyl chloride so that the method is environmental friendly. A step of hydroxy chlorination is reduced so that the method is simple in process. The conversion ratio of raw materials and the total yield of reactions are increased. The yield of the compound 6 is increased from 60% in a patent to 82%. The method is suitable for industrial production. A reaction equation is shown in the description.

Lorcaserin hydrochloride hemihydrate preparation method

The invention provides a lorcaserin hydrochloride hemihydrate preparation method. The method comprises the following steps: taking ethylamine as an initial raw material, performing an aminolysis ring-opening reaction with epoxypropane, chloridizing the material, performing friedel-Crafts alkylation cyclization on the material, splitting the material with tartaric acid, dissociating tartrate and forming hydrochloride to obtain the lorcaserin hydrochloride hemihydrate. The preparation method has the characteristics of less reaction steps, mild reaction condition, low cost of a comprehensive reagent, less three wastes, simple post-treatment and simple operation, so that the preparation method has the advantage of brand new, economy and environmental protection, high efficiency, and realization of industrial production.

A kind of products and intermediates green card color forest hydrochloride method for the preparation of (by machine translation)

The invention relates to the field of pharmaceutical chemistry, in particular relates to a diet green card color forest hydrochloride method for the preparation of intermediates thereof. The utility model is characterized in that the preparation method comprises: to the chlorobenzene ethylamine as raw materials, after sequentially acidylated protecting amino group, allyl substituted, deprotected, gram alkylate tougheness, split, a green card color forest of the hydrochloric acid salt. green card color forest hydrochloric acid of the present invention and wherein the intermediate preparation method is low in cost, simple in operation, after treatment is convenient, is an economical, can be industrial synthetic method. (by machine translation)

PROCESSES FOR THE PREPARATION OF LORCASERIN

The present invention relates to stable crystalline Form A of lorcaserin hydrochloride of Formula (IA) and processes for its preparation. The invention also relates to processes for the preparation of lorcaserin and pharmaceutically acceptable salts, solvates and hydrates thereof.