• Name

  -[2-1-NAPHTHOXY)ETHYL]BENZYLAMINE / 3-(1-NAPHTHOXY)-1-PHENYL PROPYLAMINE

• EINECS
• CAS No. 119356-76-2
• Article Data7
• CAS DataBase
• Density 1.082 g/cm³
• Solubility
• Melting Point
• Formula C₂₁H₂₃NO
• Boiling Point 454.425 °C at 760 mmHg
• Molecular Weight 305.42
• Flash Point 132.584 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms -[2-1-NAPHTHOXY)ETHYL]BENZYLAMINE / 3-(1-NAPHTHOXY)-1-PHENYL PROPYLAMINE;N,N-Dimethyl-alpha-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine;N,N-diMethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-aMine
• PSA 12.47000
• LogP 4.91160

Synthetic route

3-((4-bromonaphthalene-1-yl)oxy)-N,N-dimethyl-1-phenyl-prop-1-amine

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; acetic acid In methanol	98.2%

90-15-3

α-naphthol

936-59-4

3-chloropropiophenone

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 60 - 65℃; for 5h; Reagent/catalyst; Temperature;	97.7%

119357-32-3

C21H22ClNO

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; acetic acid In methanol	94.2%

41198-42-9

3-(naphthalen-1-yloxy)-1-phenylpropan-1-one

124-40-3

dimethyl amine

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With formic acid at 170 - 180℃; for 18h; Time;	88.5%

1445281-20-8

C20H20O4S

124-40-3

dimethyl amine

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 0 - 35℃; for 40h;

3-(naphthalen-1-yloxy)-1-phenyl-propan-1-ol

124-40-3

dimethyl amine

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Stage #1: 3-(naphthalen-1-yloxy)-1-phenyl-propan-1-ol With dmap; methanesulfonyl chloride; triethylamine In tetrahydrofuran at -5 - 0℃; Stage #2: dimethyl amine In tetrahydrofuran at 0 - 20℃; for 40h; Stage #3: With sodium hydroxide In tetrahydrofuran; water for 9 - 10h;

3646-50-2

3-Amino-3-phenylpropionic acid

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 18 h / 66 °C 2.1: 8 h / 95 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 50 °C / Inert atmosphere 3.2: 6 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / Cooling with ice 1.2: 7.5 h / 10 - 65 °C 2.1: water / 10 h / 90 °C / Cooling with ice 3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 60 °C / Cooling with ice 3.2: 9 h / 100 °C View Scheme

321-38-0

1-Fluoronaphthalene

81402-52-0

3-(dimethylamino)-3-phenylpropan-1-ol

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Stage #1: 3-(dimethylamino)-3-phenylpropan-1-ol With sodium hydride In N,N-dimethyl-formamide at 50℃; for 1.5h; Inert atmosphere; Stage #2: 1-Fluoronaphthalene In N,N-dimethyl-formamide at 100℃; for 6h;	38.6 g
Stage #1: 3-(dimethylamino)-3-phenylpropan-1-ol With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h; Cooling with ice; Stage #2: 1-Fluoronaphthalene In N,N-dimethyl-formamide at 100℃; for 9h;

100-52-7

benzaldehyde

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ammonium acetate / ethanol / 8 h / 80 °C 2.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 18 h / 66 °C 3.1: 8 h / 95 °C 4.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 50 °C / Inert atmosphere 4.2: 6 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1.1: ammonium acetate / ethanol / 6 h / 78 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / Cooling with ice 2.2: 7.5 h / 10 - 65 °C 3.1: water / 10 h / 90 °C / Cooling with ice 4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 60 °C / Cooling with ice 4.2: 9 h / 100 °C View Scheme

14593-04-5, 82769-76-4

3-amino-3-phenyl-1-propanol

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 8 h / 95 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 50 °C / Inert atmosphere 2.2: 6 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: water / 10 h / 90 °C / Cooling with ice 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 60 °C / Cooling with ice 2.2: 9 h / 100 °C View Scheme

50-00-0

formaldehyd

119357-34-5

1-phenyl-3-(naphthyl-1-oxy)propylamine

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
With formic acid In water at 90℃; for 6h;

1-phenyl-3-naphthalenyloxypropane

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 5 h / Irradiation; Reflux 2: acetone / 5 h / 50 °C / Cooling with ice 3: acetic acid; palladium 10% on activated carbon / methanol View Scheme
Multi-step reaction with 3 steps 1: dibenzoyl peroxide; N-chloro-succinimide / tetrachloromethane / 5 h / Reflux; Irradiation 2: acetone / 6 h / 50 °C / Cooling with ice 3: acetic acid; palladium 10% on activated carbon / methanol View Scheme

1-bromo-4-(3-bromo-3-phenylpropoxy)naphthalene

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 5 h / 50 °C / Cooling with ice 2: acetic acid; palladium 10% on activated carbon / methanol View Scheme

1-chloro-4-(3-chloro-3-phenylpropoxy)naphthalene

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 6 h / 50 °C / Cooling with ice 2: acetic acid; palladium 10% on activated carbon / methanol View Scheme

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate for 2h; pH=2; Cooling with ice;	85.8%

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

m

m

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol pH=2 - 3; pH-value;	84.8%

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

Dapoxetine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; (1S)-10-camphorsulfonic acid In ethanol; water at 20℃; for 15h; Temperature; Solvent; Reagent/catalyst;	76%
Multi-step reaction with 3 steps 1: ethanol; water 2: sodium hydroxide / pH >= 13 3: hydrogenchloride / acetone View Scheme

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

dapoxetine

Conditions

Conditions	Yield
With L-Tartaric acid In ethanol; water at 20℃; Cooling with ice;	37%
Multi-step reaction with 2 steps 1: ethanol; water 2: sodium hydroxide / pH >= 13 View Scheme

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

32634-68-7

(2S,3S)-di-4-toluoyltartaric acid

dapoxetine DTTA salt

Conditions

Conditions	Yield
In dichloromethane at 25 - 35℃; for 0.5h;

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

74165-69-8

ammonium bromocamphorsulfonate

(+)-N,N-Dimethyl-1-phenyl-3-(1-naphthalenyloxy) propanamine (+)-3-bromocamphor-8-sulfonate

Conditions

Conditions	Yield
In methanol; ethyl acetate

119356-76-2

N,N-dimethylamino-3-(naphthyl-1-oxy)-1-phenylprop-1-amine

147-71-7

D-tartaric acid

1448512-87-5

S-(+)-N,N-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine tartrate

Conditions

Conditions	Yield
In ethanol; water	3.5 g

N,N-Dimethyl-alpha-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine Specification