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
• Article Data: 27

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

Description

Different sources of media describe the Description of 846589-98-8 differently. You can refer to the following data:
1. In June 2012, the US FDA approved lorcaserin for chronic weight management in adult patients who are characterized as overweight or obese and have at least one comorbid, weight-related condition. Lorcaserin (also known as APD356) is the first 5-HT2C agonist approved for chronic weight management since the withdrawal of the 5-HT2C agonist fenfluramine in 1997 due to rare cases of cardiac valvulopathy. The serotonin receptor 5-HT2C is found primarily in the hypothalamus and regulates appetite and feeding behavior. Safety issues with fenfluramine were associated with poor selectivity for 5-HT2C versus 5HT2A and 5HT2B. Ring constraint afforded by the benzazepine in lorcaserin improved selectivity for 5HT2C by over 2 log units.
2. Lorcaserin (hydrochloride) (CRM) (Item No. 19247) is a certified reference material categorized as an anorectic. It also decreases oxycodone intake and has positive effects on self-administration and relapse vulnerability in the rat. Lorcaserin is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

Originator

Pharmaceuticals (United States)

Uses

Lorcaserin hydrochloride, a novel antiobesity drug, is a selective serotonin 5-HT2C receptor agonist, approved by FDA in 2012.

Definition

ChEBI: A hydrochloride obtained by reaction of lorcaserin with one equivalent of hydrochloric acid. Used as an anti-obesity drug.

Brand name

Belviq

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

• 616202-92-7 lorcaserin 
• 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 
• 119277-32-6 (3-chlorophenyl)magnesium chloride 
• 937-20-2 p-chlorophenacyl chloride 
• 20697-04-5 (R)-meta-chlorostyrene oxide 
• 20697-04-5 3-chlorostyrene oxide 

Downstream Products

• 1421747-19-4 N-Hydroxylorcaserin 
• 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 
• 1181690-72-1 (R)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone 

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.

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.

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.