1860-57-7

Basic information

• Product Name: 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride
• Synonyms: 2-(4-Benzyloxy-3-methoxyphenyl)ethylamine Hydrochloride;3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride;3-Methoxy-4-(phenylmethoxy)benzeneethanamine Hydrochloride;4-(Benzyloxy)-3-methoxyphenethylamine Hydrochloride;2-(3-METHOXY-4-PHENYLMETHOXYPHENYL)ETHANAMINE HYDROCHLORIDE;-(4-Benzyloxy-3-methoxyphenyl)ethylamine Hydrochloride
• CAS NO: 1860-57-7
• Molecular Formula: C₁₆H₁₉NO₂*ClH
• Molecular Weight: 0
• Product Categories: Amines;Aromatics
• Mol File: 1860-57-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 175-177°C
• Boiling Point: 395.1°Cat760mmHg
• Flash Point: 212.5°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.88E-06mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride(1860-57-7)
• EPA Substance Registry System: 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride(1860-57-7)

Safety Data

• Hazardous Substances Data: 1860-57-7(Hazardous Substances Data)

Usage

Description

3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride is a phenylethylamine derivative characterized by its brown sticky oil appearance. It possesses radioprotective and pharmacological properties, making it a valuable compound in various applications.

Uses

Used in Pharmaceutical Industry:
3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride is used as a radioprotective agent for its ability to shield cells and tissues from the harmful effects of radiation. This property is particularly useful in the context of cancer treatment, where radiation therapy is a common approach.
Additionally, 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride is used as a pharmacological agent due to its potential therapeutic effects. Its chemical structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Research and Development:
In the field of research and development, 3-Methoxy-4-(benzyloxy)phenethylamine Hydrochloride serves as a valuable compound for studying the properties and mechanisms of phenylethylamine derivatives. Its radioprotective and pharmacological properties make it an interesting subject for further investigation, potentially leading to the discovery of novel applications and therapeutic strategies.

InChI:InChI=1/C16H19NO2/c1-18-16-11-13(9-10-17)7-8-15(16)19-12-14-5-3-2-4-6-14/h2-8,11H,9-10,12,17H2,1H3

Synthetic route

3-methoxy-4-benzyloxy-ω-nitrostyrolene (63909-38-6, 1860-56-6) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Stage #1: 3-methoxy-4-benzyloxy-ω-nitrostyrolene With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2.5h; Reflux; Stage #2: With water In tetrahydrofuran at 0℃; Stage #3: With hydrogenchloride In diethyl ether	75%

3-Methoxy-4-benzyloxy-N-tert.-butyloxycarbonyl-phenaethylamin (23428-81-1) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Stage #1: 3-Methoxy-4-benzyloxy-N-tert.-butyloxycarbonyl-phenaethylamin With trifluoroacetic acid In dichloromethane at 0℃; for 0.666667h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water Cooling with ice; Stage #3: With hydrogenchloride In diethyl ether	64%
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 0.67 h / 0 °C 2: hydrogenchloride / diethyl ether View Scheme

2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile (1700-29-4) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
With hydrogenchloride; sodium tetrahydroborate; cobalt(II) chloride 1.) MeOH, 20 deg C, 1 h; Multistep reaction;

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96.6 percent / NaBH4 / methanol / 3 h 2: 93.5 percent / thionyl chloride / diethyl ether / 6 h 3: dimethylformamide / 168 h / Ambient temperature 4: 1.) cobaltous chloride hexahydrate, NaBH4, 2.) 3 N HCl / 1.) MeOH, 20 deg C, 1 h View Scheme
Multi-step reaction with 2 steps 1.1: ammonium acetate; acetic acid / 4 h / 90 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Reflux 2.2: 0 °C View Scheme

4-benzyloxy-3-methoxybenzyl alcohol (33693-48-0) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93.5 percent / thionyl chloride / diethyl ether / 6 h 2: dimethylformamide / 168 h / Ambient temperature 3: 1.) cobaltous chloride hexahydrate, NaBH4, 2.) 3 N HCl / 1.) MeOH, 20 deg C, 1 h View Scheme

1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene (33688-50-5) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 168 h / Ambient temperature 2: 1.) cobaltous chloride hexahydrate, NaBH4, 2.) 3 N HCl / 1.) MeOH, 20 deg C, 1 h View Scheme

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine (22231-61-4) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
With hydrogenchloride In diethyl ether

benzyl bromide (100-39-0) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 2 h / Reflux 2.1: ammonium acetate; acetic acid / 4 h / 90 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Reflux 3.2: 0 °C View Scheme

vanillin (121-33-5) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 2 h / Reflux 2.1: ammonium acetate; acetic acid / 4 h / 90 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 °C / Reflux 3.2: 0 °C View Scheme

3-Methoxytyramine (554-52-9) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / chloroform / 24 h / 20 °C 2: potassium carbonate / acetone / 12 h / Heating / reflux 3: trifluoroacetic acid / dichloromethane / 0.67 h / 0 °C 4: hydrogenchloride / diethyl ether View Scheme

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate (23699-77-6) → [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 12 h / Heating / reflux 2: trifluoroacetic acid / dichloromethane / 0.67 h / 0 °C 3: hydrogenchloride / diethyl ether View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + isobutyryl chloride (79-30-1) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]isobutyramide (1032821-89-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	96%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + butyryl chloride (141-75-3) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]butyramide (1032821-85-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	94%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + isopentanoyl chloride (108-12-3) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-3-methylbutyramide (95290-23-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	93%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + propionyl chloride (79-03-8) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]propionamide (1032821-81-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	90%
With triethylamine In dichloromethane at 0℃; for 0.5 - 1h;	90%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + propionic acid anhydride (123-62-6) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]propionamide (1032821-81-0)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	90%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-2-cyclopropanecarboxamide (1032821-96-7)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	88%

m-methoxyphenylacetic acid (1798-09-0) + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → N-(2-(4-(benzyloxy)-3-methoxyphenyl)ethyl)-2-(3-methoxyphenyl)acetamide (67237-64-3)

Conditions	Yield
Stage #1: m-methoxyphenylacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride In dichloromethane at 20℃; for 8h;	87%

bis(2-chloroethyl)(3-phenylpropyl)amine hydrochloride + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → 1-(4-(benzyloxy)-3-methoxyphenethyl)-4-(3-phenylpropyl)piperazine (925679-52-3)

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 70℃; for 5h;	83%

(3,5-dimethoxyphenyl)acetic acid (4670-10-4) + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → N-(2-(4-(benzyloxy)-3-methoxyphenyl)ethyl)-2-(3,5-dimethoxyphenyl)acetamide (1398120-89-2)

Conditions	Yield
Stage #1: (3,5-dimethoxyphenyl)acetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride In dichloromethane at 20℃; for 8h;	81%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + Cyclobutanecarbonyl chloride (5006-22-4) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-2-cyclobutanecarboxamide (1032821-99-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	79%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) + phenylacetyl chloride (103-80-0) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-2-phenylacetylamide (4876-01-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	63%

5-benzyloxy-4-methoxy-2-nitrophenylacetic acid (78792-73-1) + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → N-<4-Benzyloxy-4-methoxyphenethyl>-5-benzyloxy-4-methoxy-2-nitrophenylacetamide (99613-09-9)

Conditions	Yield
With sodium hydroxide In chloroform; water for 4h; Ambient temperature;	56%

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → 1-<5-benzyloxy-4-methoxy-2-nitrobenzyl>-7-benzyloxy-6-methoxy-3,4-dihydroisoquinoline (99612-79-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / 2 N NaOH / CHCl3; H2O / 4 h / Ambient temperature 2: 72 percent / POCl3 / acetonitrile / 2 h / Heating View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → 1-<5-Benzyloxy-4-methoxy-2-nitrobenzyl>-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline (99612-81-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 56 percent / 2 N NaOH / CHCl3; H2O / 4 h / Ambient temperature 2: 72 percent / POCl3 / acetonitrile / 2 h / Heating 3: 81 percent / NaBH4 / methanol / 2 h / Ambient temperature View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-[2,3-dihydrobenzo[b]furan-7-yl]cyclopropane carboxamide

Conditions	Yield
With thionyl chloride; triethylamine In water; ethyl acetate

1-(1-naphthyl)cyclopropane carbonyl chloride + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-1-(1-naphthyl)cyclopropane carboxamide

Conditions	Yield
With triethylamine In ethyl acetate

C16H14O6S (1233354-44-3) + [2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → C32H33NO8S (1233354-57-8)

Conditions	Yield
With triethylamine In methanol for 5h; Reflux;

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → (S)-2-hydroxy-3,11-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine (1398121-01-1)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux 3.1: [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3.2: 20 °C / pH 8 4.1: formic acid / 2 h / 25 °C 5.1: hydrogenchloride / ethanol; water / Reflux 5.2: 0 °C / pH 9 View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → (S)-2-hydroxy-3,9,11-trimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo-[a,g]quinolizine (1398121-03-3)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux 3.1: [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3.2: 20 °C / pH 8 4.1: formic acid / 2 h / 50 °C 5.1: hydrogenchloride / ethanol; water / Reflux 5.2: 0 °C / pH 9 View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → 7-(benzyloxy)-1-((3,5-dimethoxyphenyl)methyl)-6-methoxy-3,4-dihydroisoquinoline (1398120-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → C25H27NO3 (1422431-23-9)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux 3.1: [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3.2: 20 °C / pH 8 View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → (S)-7-(benzyloxy)-1-((3,5-dimethoxyphenyl)methyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (1398120-87-0)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux 3.1: [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3.2: 20 °C / pH 8 View Scheme

[2-(4-benzyloxy-3-methoxyphenyl)ethyl]amine hydrochloride (1860-57-7) → (S)-2-benzyloxy-3,11-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine (1398120-70-1)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C 1.2: 8 h / 20 °C 2.1: trichlorophosphate / acetonitrile / 0.5 h / Reflux 3.1: [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2, 3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]-ruthenium; formic acid; triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3.2: 20 °C / pH 8 4.1: formic acid / 2 h / 25 °C View Scheme

Upstream product

• 23699-77-6 tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate 
• 554-52-9 3-Methoxytyramine 
• 121-33-5 vanillin 
• 100-39-0 benzyl bromide 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 33688-50-5 1-(benzyloxy)-4-(chloromethyl)-2-methoxybenzene 
• 33693-48-0 4-benzyloxy-3-methoxybenzyl alcohol 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1700-29-4 2-(4-(benzyloxy)-3-methoxyphenyl)acetonitrile 
• 23428-81-1 3-Methoxy-4-benzyloxy-N-tert.-butyloxycarbonyl-phenaethylamin 

Downstream Products

• 1032821-81-0 N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]propionamide 
• 67237-64-3 N-(2-(4-(benzyloxy)-3-methoxyphenyl)ethyl)-2-(3-methoxyphenyl)acetamide 
• 1398120-70-1 (S)-2-benzyloxy-3,11-dimethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizine 
• 1398120-72-3 (S)-2-(benzyloxy)-3,9,11-trimethoxytetrahydroprotoberberine 
• 753397-09-0 7-benzyloxy-6-methoxy-1-(3-methoxy-benzyl)-3,4-dihydro-isoquinoline 
• 19886-92-1 1-ethyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 1233354-57-8 C₃₂H₃₃NO₈S 
• 1032821-99-0 N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-2-cyclobutanecarboxamide 
• 925679-52-3 1-(4-(benzyloxy)-3-methoxyphenethyl)-4-(3-phenylpropyl)piperazine 
• 99612-81-4 1-<5-Benzyloxy-4-methoxy-2-nitrobenzyl>-7-benzyloxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 99612-79-0 1-<5-benzyloxy-4-methoxy-2-nitrobenzyl>-7-benzyloxy-6-methoxy-3,4-dihydroisoquinoline 
• 99613-09-9 N-<4-Benzyloxy-4-methoxyphenethyl>-5-benzyloxy-4-methoxy-2-nitrophenylacetamide 

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