• Name

  1-[[2-(4-Chlorophenyl)ethyl]amino]-2-chloropropane

• EINECS
• CAS No. 953789-37-2
• Article Data12
• CAS DataBase
• Density
• Solubility
• Melting Point
• Formula C11H15 Cl2 N . Cl H
• Boiling Point
• Molecular Weight 268.614
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 1-[[2-(4-Chlorophenyl)ethyl]amino]-2-chloropropane;1-[[2-(4-Chlorophenyl)ethyl]amino]-2-chloropropane Hydrochloride;2-Chloro-N-(4-chlorophenethyl)propan-1-aMine hydrochloride;BenzeneethanaMine, 4-chloro-N-(2-chloropropyl)-, hydrochloride (1:1);2-chloro-N-(4-chlorophenethyl)propan-1-aMin hydrochloride;Lorcaserin interMediate;Lorcaserin iMpurity B;2-chloro-N-(4-chlorophenethyl)propan-1-aMiniuM chloride
• PSA 12.03000
• LogP 4.29230

Synthetic route

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

953789-37-2

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

Conditions

Conditions	Yield
With aluminum (III) chloride; sodium tetrahydroborate; chloro-trimethyl-silane In tetrahydrofuran at 70℃; for 24h; Inert atmosphere;	96%

847063-13-2

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

953789-37-2

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

Conditions

Conditions	Yield
With thionyl chloride In N,N-dimethyl acetamide; toluene at 50 - 65℃; for 3h; Inert atmosphere;	88.3%
With thionyl chloride In toluene at 70℃; for 10h;	85%
With thionyl chloride In N,N-dimethyl acetamide; toluene at 45 - 60℃;	81.3%

1030624-41-9

1-((4-chlorophenethyl)amino)propan-2-ol hydrochloride

953789-37-2

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

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl acetamide In toluene at 50 - 65℃; for 2.5h; Product distribution / selectivity;	85.82%
With thionyl chloride In N,N-dimethyl acetamide; toluene at 50 - 65℃; Inert atmosphere;	85.66%
With thionyl chloride at 50 - 62℃; for 2h; Product distribution / selectivity; Neat (no solvent);	69.52%

N-(2-(4-chlorophenyl)ethyl)-4-methyl-N-(2-chloropropyl)benzenesulfonamide

953789-37-2

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

Conditions

Conditions	Yield
With sulfuric acid In water at 120℃; for 2h; Temperature; Reagent/catalyst;	84.7%

156-41-2

4-chlorophenylethylamine

953789-37-2

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium triflate / methanol / 6.5 h / 30 - 60 °C 2: N,N-dimethyl-formamide; thionyl chloride / toluene / 2 h / 45 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 20 - 60 °C / Inert atmosphere 2: thionyl chloride / N,N-dimethyl acetamide; toluene / 45 - 60 °C View Scheme

1030624-36-2

2-(4-chlorophenyl)-N-(2-hydroxypropyl)acetamide

953789-37-2

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

Conditions

Conditions	Yield
Stage #1: 2-(4-chlorophenyl)-N-(2-hydroxypropyl)acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 65℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene at 30 - 40℃; for 0.5h;

140-53-4

p-chlorobenzyl cyanide

953789-37-2

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 55 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 20 - 60 °C / Inert atmosphere 3: thionyl chloride / N,N-dimethyl acetamide; toluene / 45 - 60 °C View Scheme

1-(4-chlorophenyl)-2-((2-hydroxypropyl)amino)ethane-1-one

953789-37-2

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / 2-methyltetrahydrofuran / 0.25 h / 15 - 20 °C 1.2: 10 h / 60 °C 2.1: thionyl chloride / toluene / 10 h / 70 °C View Scheme

937-20-2

p-chlorophenacyl chloride

953789-37-2

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium carbonate / ethanol / 8 h / 60 °C 2.1: sodium tetrahydroborate / 2-methyltetrahydrofuran / 0.25 h / 15 - 20 °C 2.2: 10 h / 60 °C 3.1: thionyl chloride / toluene / 10 h / 70 °C View Scheme

1875-88-3

2-(4-Chlorophenyl)ethanol

953789-37-2

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide / 91 - 96 °C / 517.55 - 1807.68 Torr 3: thionyl chloride; N,N-dimethyl acetamide / toluene / 50 - 65 °C View Scheme

2-(4-chlorophenyl)-N-(2-chloropropyl)acetamide

953789-37-2

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

Conditions

Conditions	Yield
Stage #1: 2-(4-chlorophenyl)-N-(2-chloropropyl)acetamide With sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex at 60℃; Stage #2: With hydrogenchloride In water for 0.5h; Reflux;	315.2 g

953789-37-2

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

616201-80-0

(+/-)-Lorcaserin

Conditions

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%

847063-13-2

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

953789-37-2

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

1-((4-chlorophenethyl)(1-((4-chlorophenethyl)amino)propan-2-yl)amino)propan-2-ol

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70 - 75℃; for 5h;	22.3%

953789-37-2

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

95-50-1

1,2-dichloro-benzene

616201-80-0

(+/-)-Lorcaserin

Conditions

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;

953789-37-2

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

846589-98-8

Lorcaserin hydrochloride

Conditions

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

953789-37-2

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1,2-dichloro-benzene / 3 h / 125 - 130 °C 2: L-Tartaric acid / acetone; water / 0.5 h / 45 - 50 °C View Scheme

953789-37-2

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

2C11H14ClN*C4H6O6

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum oxide / 1,2-dichloro-benzene / 130 - 140 °C / Inert atmosphere 2: acetone; water / 0 - 55 °C View Scheme

953789-37-2

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum oxide / 1,2-dichloro-benzene / 130 - 140 °C / Inert atmosphere 2: acetone; water / 0 - 55 °C 3: potassium carbonate / water; ethyl acetate / 0.5 h / 25 - 30 °C View Scheme

953789-37-2

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

lorcaserin

Conditions

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-benzene at 126℃; for 16h; Temperature; Friedel-Crafts Alkylation; Inert atmosphere; Large scale;

1-[[2-(4-Chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride Chemical Properties