846589-98-8

Basic information

• Product Name: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE
• Synonyms: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE;LORCASERIN HCL;Lorcaserin hydrochloride;(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride;(1R)-8-chloro-1-Methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;R Lorcaserin hydrochloride;lorcaserin hydrochloride (APD-356);(R)-8-Chloro-1-Methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride
• CAS NO: 846589-98-8
• Molecular Formula: C₁₁H₁₄ClN*ClH
• Molecular Weight: 232
• EINECS: 1592732-453-0
• Product Categories: APIs;5-HT 2c receptor agonist;Inhibitors
• Mol File: 846589-98-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE(846589-98-8)
• EPA Substance Registry System: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE(846589-98-8)

Safety Data

• Hazardous Substances Data: 846589-98-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Lorcaserin hydrochloride is used as an antiobesity drug for the treatment of chronic weight management in adult patients who are overweight or obese and have at least one weight-related comorbid condition. It acts as a selective serotonin 5-HT2C receptor agonist, helping to regulate appetite and feeding behavior.
Used in Research and Forensic Applications:
Lorcaserin (hydrochloride) (CRM) is a certified reference material categorized as an anorectic. It is used in research and forensic applications to study its effects on decreasing oxycodone intake and its positive impact on self-administration and relapse vulnerability in rats. Lorcaserin is regulated as a Schedule IV compound in the United States, ensuring its proper use and distribution in these applications.

Originator

Pharmaceuticals (United States)

Side effects

Lorcaserin hydrochloride (Belviq) is a serotonin 2C receptor agonist that causes weight loss by causing appetite suppression.It appears to have fewer adverse effects than orlistat,although long-term safety data are limited. The recommended dosage is 10mg twice daily. Lorcaserin should be discontinued if patients do not lose 5% of their body weight in 12 weeks. The efficacy of lorcaserin appears similar to that of orlistat (mean difference in weight loss between active and placebo-treated groups approximately 3-4 kg).Common side effects include nausea, headache,dizziness, nasopharyngitis, and fatigue. Lorcaserin may increasethe risk of symptomatic hypoglycemia in patients with type 2 diabetes on oral agents, necessitating a reduction in the dose of diabetes medications. Lorcaserin should not be used in individuals with creatinine clearance <30 mL/minute. It is contraindicated during pregnancy. In addition, lorcaserin should not be used with other serotonergic drugs (e.g., selective serotonin reuptake inhibitors,selective serotonin-norepinephrine reuptake inhibitors, bupropion[Wellbutrin], tricyclic antidepressants,and monamine oxidase inhibitors)because of the theoretical potential for serotonin syndrome.https://www.accessdata.fda.govhttps://medlineplus.gov

Synthetic route

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Stage #1: 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate With sodium hydroxide In dichloromethane; water at 10 - 30℃; for 1h; Stage #2: With hydrogenchloride In ethyl methyl ether at 0 - 10℃; pH=1.5 - 2.5;	98.6%
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; dichloromethane; tert-butyl alcohol 1.2: 90 - 100 °C / Inert atmosphere 1.3: 10 h / 20 °C 2.1: sodium hydroxide / water / 0.17 h / 20 °C 2.2: 0.08 h / 20 °C View Scheme

lorcaserin → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
With hydrogenchloride In methanol; water at 0 - 5℃; Solvent; Concentration;	98%
With hydrogenchloride In water; ethyl acetate pH=<= 5; pH-value; Large scale;	98%
With hydrogenchloride In dichloromethane; water at 20℃; for 0.166667h;	97%

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Stage #1: (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate With potassium carbonate In water; ethyl acetate at 15℃; Large scale; Stage #2: With hydrogenchloride In water; ethyl acetate pH=<= 5; Temperature; Large scale;	98%
Stage #1: (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate With potassium carbonate In water; ethyl acetate at 20 - 25℃; for 0.5 - 0.666667h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃;	89.9%

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Stage #1: (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate With potassium carbonate In water; ethyl acetate at 20℃; for 1h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 8℃; for 2h; Concentration;	90.5%
Stage #1: (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate With potassium carbonate In dichloromethane; water at 20℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane; water for 4h; Solvent; Reagent/catalyst; Cooling with ice;	35.3%
Stage #1: (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate With sodium hydroxide In water at 20℃; for 0.166667h; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20℃; for 0.0833333h;	3.88 g

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Stage #1: bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate With potassium carbonate In water; ethyl acetate at 20 - 25℃; for 0.5 - 0.666667h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃; for 3.5 - 4h; (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;	89.9%
Stage #1: bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate With sodium hydroxide In dichloromethane; water at 25℃; for 0.5h; pH=10; Stage #2: With hydrogenchloride In ethyl acetate at 0℃; for 2.5h; pH=2;	2.25 g
Stage #1: bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate With potassium carbonate In water at 10 - 25℃; for 0.333333h; Stage #2: With hydrogenchloride In water; ethyl acetate at 0 - 5℃; Temperature;	21.4 g

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Stage #1: 8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate With potassium carbonate In water; ethyl acetate at 20 - 25℃; for 50.6667h; Stage #2: With hydrogenchloride In ethyl acetate at 0 - 5℃; for 3.5 - 4h;	89.9%

N-allyl-N-(4-chlorophenethyl)carbamic acid tert-butyl ester → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 5 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 3: acetone; water / 3 h / 50 °C / Large scale 4: potassium carbonate / water 5: hydrogenchloride / ethyl acetate; ethanol / 20 °C / pH 2 View Scheme
Multi-step reaction with 4 steps 1.1: hydrogenchloride / ethyl acetate / 20 °C 2.1: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C 3.1: acetone; water / 3 h / 50 °C 3.2: 5 h / 0 - 5 °C / Reflux 4.1: sodium hydroxide / dichloromethane; water / 0.5 h / 25 °C / pH 10 4.2: 2.5 h / 0 °C / pH 2 View Scheme
Multi-step reaction with 4 steps 1.1: dichloromethane / 25 °C 2.1: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C 3.1: acetone; water / 3 h / 50 °C 3.2: 5 h / 0 - 5 °C / Reflux 4.1: sodium hydroxide / dichloromethane; water / 0.5 h / 25 °C / pH 10 4.2: 2.5 h / 0 °C / pH 2 View Scheme
Multi-step reaction with 4 steps 1: aluminum (III) chloride / chlorobenzene / 110 °C 2: acetone / 3 h / 50 °C 3: potassium carbonate / water / pH 8-9 4: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C / pH 1-2 View Scheme

N-(4-chlorophenylethyl)propyl-2-ene-1-amine trifluoroacetate → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 110 °C 2.1: acetone; water / 3 h / 50 °C 2.2: 5 h / 0 - 5 °C / Reflux 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / 25 °C / pH 10 3.2: 2.5 h / 0 °C / pH 2 View Scheme

C13H15ClF3NO → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / methanol / 3 h / 60 °C 2.1: aluminum (III) chloride / 1,2-dichloro-benzene / 90 °C 3.1: acetone; water / 3 h / 50 °C 3.2: 5 h / 0 - 5 °C / Reflux 4.1: sodium hydroxide / dichloromethane; water / 0.5 h / 25 °C / pH 10 4.2: 2.5 h / 0 °C / pH 2 View Scheme

N-(4-chlorophenylethyl)propyl-2-ene-1-amine (1247548-14-6) → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 90 °C 2.1: acetone; water / 3 h / 50 °C 2.2: 5 h / 0 - 5 °C / Reflux 3.1: sodium hydroxide / dichloromethane; water / 0.5 h / 25 °C / pH 10 3.2: 2.5 h / 0 °C / pH 2 View Scheme

1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane (847063-13-2) → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 2 h / 45 - 60 °C 2.1: aluminum (III) chloride / 1,2-dichloro-benzene / 3 h / 125 - 130 °C 3.1: L-Tartaric acid / acetone; water / 0.5 h / 45 - 50 °C 4.1: potassium carbonate / water / 0.33 h / 10 - 25 °C 4.2: 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 10 h / 70 °C 2.1: aluminum (III) chloride / 1,2-dichloro-benzene / 10 h / 140 °C 3.1: L-Tartaric acid / ethanol; water / 80 °C 3.2: pH 12 3.3: 1 h / 5 - 10 °C View Scheme

1-((2-(4-chlorophenyl)ethyl)amino)-2-chloropropane hydrochloride (953789-37-2) → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1,2-dichloro-benzene / 3 h / 125 - 130 °C 2.1: L-Tartaric acid / acetone; water / 0.5 h / 45 - 50 °C 3.1: potassium carbonate / water / 0.33 h / 10 - 25 °C 3.2: 0 - 5 °C View Scheme

(R)-N-tert-butoxycarbonyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (851477-82-2) → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
With hydrogenchloride In methanol; water	1.8 g

2-(2-bromo-4-chlorophenyl)ethan-1-amine (1202889-65-3) → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ethanol / 0.5 h 1.2: 1 h / Cooling with ice 2.1: methanol / 3 h 3.1: triethylamine / acetonitrile / 10 h / 80 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen; dimethylsulfide; thiourea / quinoline / 4 h / 3750.38 Torr 5.1: hydrogenchloride / methanol; water View Scheme

C11H13BrClN → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol / 3 h 2: triethylamine / acetonitrile / 10 h / 80 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen; dimethylsulfide; thiourea / quinoline / 4 h / 3750.38 Torr 4: hydrogenchloride / methanol; water View Scheme

C16H21BrClNO2 → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / 10 h / 80 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen; dimethylsulfide; thiourea / quinoline / 4 h / 3750.38 Torr 3: hydrogenchloride / methanol; water View Scheme

(±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (1431697-94-7) → Lorcaserin hydrochloride (846589-98-8) + (S)-8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepine hydrochloride

Conditions	Yield
With Chiralpak IA column In methanol; ethanol; hexane; diethylamine at 20℃; Temperature; Resolution of racemate;

(R)-2-chloro-N-(2-(3-chlorophenyl)propyl)acetamide → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: borane-THF / tetrahydrofuran / 15 h / 25 °C 1.2: 1 h / 5 - 25 °C 2.1: aluminum (III) chloride / neat (no solvent) / 150 °C 3.1: hydrogenchloride / diethyl ether; water; dichloromethane View Scheme

(R)-N-(2-(3-chlorophenyl)propyl)-N-(2,2-dimethoxyethyl)-4-methyl benzenesulfonamide → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 2: hydrogenchloride; platinum(IV) oxide; hydrogen / water; methanol / 48 h / 25 °C / 3750.38 Torr 3: phenol; hydrogen bromide; propionic acid / 6 h / Reflux 4: hydrogenchloride / diethyl ether; water; dichloromethane View Scheme

N-(2-(3-chlorophenyl)propyl)-N-(2,2-dimethoxyethyl)-4-methylbenzene sulfonamide → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride; platinum(IV) oxide; hydrogen / water; methanol / 48 h / 25 °C / 3750.38 Torr 2: phenol; hydrogen bromide; propionic acid / 6 h / Reflux 3: hydrogenchloride / diethyl ether; water; dichloromethane View Scheme

(R)-2-(3-chlorophenyl)propan-2-amine hydrochloride salt → Lorcaserin hydrochloride (846589-98-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydroxide / water 2.1: sodium carbonate / dichloromethane / 0.25 h / 5 - 10 °C 2.2: 25 °C 3.1: borane-THF / tetrahydrofuran / 15 h / 25 °C 3.2: 1 h / 5 - 25 °C 4.1: aluminum (III) chloride / neat (no solvent) / 150 °C 5.1: hydrogenchloride / diethyl ether; water; dichloromethane View Scheme
Multi-step reaction with 7 steps 1: sodium hydroxide / water 2: potassium carbonate / N,N-dimethyl-formamide / 120 °C / Inert atmosphere 3: pyridine / dichloromethane / 2.5 h / 0 - 20 °C 4: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 5: hydrogenchloride; platinum(IV) oxide; hydrogen / water; methanol / 48 h / 25 °C / 3750.38 Torr 6: phenol; hydrogen bromide; propionic acid / 6 h / Reflux 7: hydrogenchloride / diethyl ether; water; dichloromethane View Scheme

Lorcaserin hydrochloride (846589-98-8) + acrylonitrile (107-13-1) → (R)-3-(8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)propanenitrile

Conditions	Yield
With sodium In methanol at 55℃; for 12h; Inert atmosphere;	96%

Lorcaserin hydrochloride (846589-98-8) + benzoic acid (65-85-0) → C11H14ClN*ClH*C7H6O2

Conditions	Yield
In acetone Solvent;	94.7%

Lorcaserin hydrochloride (846589-98-8) + 2-Chloroethyl chloroformate (627-11-2) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 3-carboxylic acid 2-chloroethyl ester

Conditions	Yield
Stage #1: Lorcaserin hydrochloride With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 2-Chloroethyl chloroformate In dichloromethane at 0℃; for 2h;	94.5%

Lorcaserin hydrochloride (846589-98-8) + D-(+)-camphoric acid (124-83-4) → (R)-lorcaserin hydrochloride (1R,3S)-(+)-camphoric acid

Conditions	Yield
at 20 - 25℃; Concentration; Temperature; Reflux;	81%

Lorcaserin hydrochloride (846589-98-8) + 1,1'-carbonyldiimidazole (530-62-1) + 2-(Diethylamino)ethanol (100-37-8) → (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-3-carboxylic acid 2-(diethylamino)ethyl ester

Conditions	Yield
Stage #1: 1,1'-carbonyldiimidazole; 2-(Diethylamino)ethanol In dichloromethane at 0 - 20℃; for 5.16667h; Inert atmosphere; Stage #2: Lorcaserin hydrochloride In dichloromethane at 20℃;	80.4%

Lorcaserin hydrochloride (846589-98-8) + 1-Bromo-4-phenylbutane (13633-25-5) → C21H26ClN

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 90℃; for 18h; Sealed tube;	70%

Lorcaserin hydrochloride (846589-98-8) + oxalic acid (144-62-7) → (R)-lorcaserin hydrochloride oxalic acid

Conditions	Yield
Stage #1: Lorcaserin hydrochloride With sodium hydroxide In water pH=10; Stage #2: oxalic acid With hydrogenchloride In ethyl acetate at 20 - 25℃; Concentration; Reagent/catalyst; pH-value; Temperature; Solvent;	68%

Lorcaserin hydrochloride (846589-98-8) + trifluoroacetic anhydride (407-25-0) → (1R)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (616202-89-2)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 3h;

Lorcaserin hydrochloride (846589-98-8) + acetyl chloride (75-36-5) → (R)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone (1181690-72-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;

Lorcaserin hydrochloride (846589-98-8) + methoxypropionyl chloride (4244-59-1) → 3-methoxy-1-((R)-1-methyl-8-(4-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)phenyl)-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)propan-1-one (1181691-01-9)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h;

Lorcaserin hydrochloride (846589-98-8) → (R)-8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepine-3(2H)-sulfonic acid

Conditions	Yield
With human sulfotransferase; 3′-phosphoadenosine 5′-phosphosulfate In aq. buffer at 37℃; for 0.05h; pH=7.5; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 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 
• 616202-92-7 lorcaserin 
• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate 
• 167886-56-8 1-[2-(tert-butoxycarbonylamino)ethyl]4-chlorobenzene 
• 156-41-2 4-chlorophenylethylamine 
• 847063-13-2 1-[[2-(4-chlorophenyl)ethyl]amino]-2-hydroxypropane 
• 953789-37-2 1-[[2-(4-chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride 
• 851477-82-2 (R)-N-tert-butoxycarbonyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 1202889-65-3 2-(2-bromo-4-chlorophenyl)ethan-1-amine 
• 1431697-94-7 (±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 937-20-2 p-chlorophenacyl chloride 

Downstream Products

• 1181690-72-1 (R)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone 
• 1181691-01-9 3-methoxy-1-((R)-1-methyl-8-(4-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)phenyl)-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)propan-1-one 
• 1421747-19-4 N-Hydroxylorcaserin 

Relevant articles and documents

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.

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.

MODIFIED-RELEASE DOSAGE FORMS OF 5-HT2C AGONISTS USEFUL FOR WEIGHT MANAGEMENT

The present invention relates to methods for weight management that utilize modified-release dosage forms comprising (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine salts and crystalline forms thereof. The present invention further relates to (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine salts, crystalline forms thereof and modified-release dosage forms comprising them.

A new enantioselective synthesis of antiobesity drug lorcaserin

A simple and efficient enantioselective synthesis of anti-obesity drug lorcaerin starting from easily accessible 3-chlorostyrene oxide has been described for the first time employing hydrolytic kinetic resolution as a source of chirality. The protocol might also be useful in the synthesis of structural variants of lorcaserin.

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

Synthesis of enantiopure antiobesity drug lorcaserin

Acylation of enantiomerically pure (R)-2-(3-chlorophenyl)propan-1-amine using chloroacetyl chloride, followed by borane reduction and aluminum chloride catalyzed cyclization yielded enantiopure lorcaserin.

Liquid chromatographic separation and thermodynamic investigation of lorcaserin hydrochloride enantiomers on immobilized amylose–based chiral stationary phase

A novel liquid chromatographic method was developed for enantiomeric separation of lorcaserin hydrochloride on Chiralpak IA column containing chiral stationary phase immobilized with amylose tris (3.5-dimethylphenylcarbamate) as chiral selector. Baseline separation with resolution greater than 4 was achieved using mobile phase containing mixture of n-hexane/ethanol/methanol/diethylamine (95:2.5:2.5:0.1, v/v/v/v) at a flow rate of 1.2?mL/min. The limit of detection and limit of quantification of the S-enantiomer were found to be 0.45 and 1.5?μg/mL, respectively; the developed method was validated as per ICH guideline. The influence of column oven temperatures studied in the range of 20°C to 50°C on separation was studied; from this, retention, separation, and resolution were investigated. The thermodynamic parameters ΔH°, ΔS°, and ΔG° were evaluated from van't Hoff plots,(Ink′ versus 1/T) and used to explain the strength of interaction between enantiomers and immobilized amylose–based chiral stationary phase.

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.

A green card color lin hydrochloride semi-hydrate crystal preparation method (by machine translation)

The invention belongs to the field of the preparation of the crystalline form of the compound in a green card color lin hydrochloride semi-hydrate crystal preparation method, the method comprises the following steps: (1) the green card color lin hydrochloric acid salt can be dissolved in the organic solvent after 1st, adding water, stirring, concentrated to remove the solvent, to obtain the oily matter; (2) the oil-like to 2nd is added in the organic solvent, stirring, to obtain a green card color lin hydrochloride semi-hydrate crystalline form. The method without the control of the hydrogen chloride gas into the amount and does not need to realize the process by heating the crystal, with easy control of reaction conditions, moderate, high yield and good quality of the products and the like. (by machine translation)

COCRYSTAL OF LORCASERIN, PREPARATION METHODS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF (AS AMENDED)

The present invention relates to a new type of eutectic crystal of lorcaserin hydrochloride and benzoic acid. Compared with the prior art, the eutectic crystal has the improved properties of good stability, low solubility, and being suitable for the application of controlled-release preparation. The present invention also relates to a method for preparing the eutectic crystal, a pharmaceutical composition thereof and the use thereof in the manufacture of drugs for treating and/or preventing diseases associated with 5HT2C.