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CAS No.: 846589-98-8
Name: (R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE
Article Data: 27
Molecular Structure:
Molecular Structure of 846589-98-8 ((R)-1H-3-BENZAZEPINE,8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-,HYDROCHLORIDE)
Formula: C11H14 Cl N . Cl H
Molecular Weight: 232.153
Synonyms: 1H-3-Benzazepine,8-chloro-2,3,4,5-tetrahydro-1-methyl-, hydrochloride, (1R)- (9CI);(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride;(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride; APD356; Lorcaserin hydrochloride
EINECS: 1592732-453-0
PSA: 12.03000
LogP: 3.72000
Related products
Synthetic route

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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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
1247548-14-6

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

846589-98-8

Lorcaserin hydrochloride

Conditions
ConditionsYield
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
Raw Materials
616201-80-0
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Chemistry

Structure of (R)-1h-3-benzazepine,8-chloro-2,3,4,5-tetrahydro-1-methyl-,hydrochloride (CAS NO.846589-98-8):

IUPAC Name:  (1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
Molecular Formula : C11H15Cl2N
Molecular Weight:232

Specification

 (R)-1h-3-benzazepine,8-chloro-2,3,4,5-tetrahydro-1-methyl-,hydrochloride ,its cas register number is 846589-98-8. It also can be called  (1R)-8-Chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine hydrochloride and Lorcaserin hydrochloride .