2970-95-8

Usage

Synthesis Reference(s)

Synthesis, p. 495, 1984 DOI: 10.1055/s-1984-30879

InChI:InChI=1/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3

Synthetic route

N,N-dimethyl-3,4-dimethoxyphenylglyoxamide (127901-47-7) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;	88%

1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone (33061-24-4) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 3.25h;	80%

1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone hydrochloride (33061-25-5) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
With ethanol; platinum Hydrogenation;

1,2-dimethoxybenzene (91-16-7) + N,N-dimethyl-glycine nitrile; hydrochloride (3976-11-2) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
(i), (ii) NaBH4; Multistep reaction;

dimethylaminomethyltributyltin (26285-62-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
With n-butyllithium 1.) hexane, THF, -78 deg C, 15 min, 2.) -78 deg C, 2 h; Yield given. Multistep reaction;

1,2-dimethoxybenzene (91-16-7) + ClO2 → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 42 percent / p-toluenesulfonic acid / 1,2-dichloro-ethane / 1 h / Heating 2: sodium metaperiodate / H2O; methanol / 15 h / Ambient temperature 3: acetic anhydride / 0.5 h / Heating 4: 88 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme

2-(3,4-Dimethoxy-phenyl)-2-methanesulfinyl-N,N-dimethyl-acetamide (127901-45-5) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic anhydride / 0.5 h / Heating 2: 88 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme

2-(3,4-Dimethoxy-phenyl)-N,N-dimethyl-2-methylsulfanyl-acetamide (127901-39-7) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium metaperiodate / H2O; methanol / 15 h / Ambient temperature 2: acetic anhydride / 0.5 h / Heating 3: 88 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme

2-methoxy-phenol (90-05-1) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 55 °C 2.1: aluminum (III) chloride / dichloromethane / 0.58 h / -5 - 0 °C 2.2: 1 h / -5 - 0 °C 3.1: bromine / chloroform / 3 h / 20 °C 4.1: ethanol / 0.67 h / 0 - 5 °C 5.1: sodium tetrahydroborate / methanol / 3.25 h / 20 °C View Scheme

1,2-dimethoxybenzene (91-16-7) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: aluminum (III) chloride / dichloromethane / 0.58 h / -5 - 0 °C 1.2: 1 h / -5 - 0 °C 2.1: bromine / chloroform / 3 h / 20 °C 3.1: ethanol / 0.67 h / 0 - 5 °C 4.1: sodium tetrahydroborate / methanol / 3.25 h / 20 °C View Scheme

1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / chloroform / 3 h / 20 °C 2: ethanol / 0.67 h / 0 - 5 °C 3: sodium tetrahydroborate / methanol / 3.25 h / 20 °C View Scheme

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone (1835-02-5) → 1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 0.67 h / 0 - 5 °C 2: sodium tetrahydroborate / methanol / 3.25 h / 20 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → 2-(3',4'-dimethoxyphenyl)-6,7-dimethoxynaphthalene (19611-17-7)

Conditions	Yield
With hydrogenchloride

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → dimethyl-(2,3,7,8-tetramethoxy-5H-dibenzo[a,d]cyclohepten-5-ylmethyl)-amine (571-91-5)

Conditions	Yield
With hydrogenchloride

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → C12H18NO3(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 85℃; for 0.75h;

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]dimethylamine (1616788-82-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]methylcarbamic acid ethyl ester (1616788-83-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → 4-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)-2-methylbutyric acid ethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: boron trifluoride diethyl etherate / ethyl acetate / 3.25 h / 0 - 20 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl]methylcarbamic acid ethyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: boron trifluoride diethyl etherate / ethyl acetate / 3.25 h / 0 - 20 °C 5: potassium carbonate / acetone / 1 h / 20 - 45 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl]methylamine

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: boron trifluoride diethyl etherate / ethyl acetate / 3.25 h / 0 - 20 °C 5: potassium carbonate / acetone / 1 h / 20 - 45 °C 6: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → 6,7-dimethoxy-4-(4-methoxyphenyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (23330-76-9, 23367-60-4, 66395-91-3, 110841-21-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: boron trifluoride diethyl etherate / ethyl acetate / 3.25 h / 0 - 20 °C 5: potassium carbonate / acetone / 1 h / 20 - 45 °C 6: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C 7: formaldehyd / acetic acid / 2 h / 90 °C / Inert atmosphere View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3,4-dimethoxyphenyl)-2-phenoxyethyl]methylamine (1616788-86-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → [2-(3,4-dimethoxyphenyl)-2-phenoxyethyl]methylamine (1616788-87-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C 5: formaldehyd / acetic acid / 1 h / 90 °C / Inert atmosphere View Scheme

1-(3, 4-dimethoxyphenyl)-2-dimethylaminoethanol (2970-95-8) → 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol (1616781-25-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium hydroxide / dimethyl sulfoxide / 0.75 h / 85 °C 2: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 - 120 °C 3: sodium hydrogencarbonate / toluene / 2.5 h / 120 °C 4: sodium hydroxide / dimethyl sulfoxide / 6 h / 125 °C 5: formaldehyd / acetic acid / 1 h / 90 °C / Inert atmosphere 6: boron trifluoride diethyl etherate / ethyl acetate / 2.25 h / 0 - 20 °C View Scheme

Upstream product

• 33061-25-5 1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone hydrochloride 
• 91-16-7 1,2-dimethoxybenzene 
• 3976-11-2 N,N-dimethyl-glycine nitrile; hydrochloride 
• 26285-62-1 dimethylaminomethyltributyltin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 33061-24-4 1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanone 
• 90-05-1 2-methoxy-phenol 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 127901-39-7 2-(3,4-Dimethoxy-phenyl)-N,N-dimethyl-2-methylsulfanyl-acetamide 
• 127901-45-5 2-(3,4-Dimethoxy-phenyl)-2-methanesulfinyl-N,N-dimethyl-acetamide 
• 127901-47-7 N,N-dimethyl-3,4-dimethoxyphenylglyoxamide 

Downstream Products

• 19611-17-7 2-(3',4'-dimethoxyphenyl)-6,7-dimethoxynaphthalene 
• 1616788-82-9 [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]dimethylamine 
• 1616788-83-0 [2-(3, 4-dimethoxyphenyl)-2-phenoxyethyl]methylcarbamic acid ethyl ester 
• 23330-76-9 6,7-dimethoxy-4-(4-methoxyphenyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline 
• 1616788-86-3 [2-(3,4-dimethoxyphenyl)-2-phenoxyethyl]methylamine 
• 1616788-87-4 [2-(3,4-dimethoxyphenyl)-2-phenoxyethyl]methylamine 
• 1616781-25-9 4-(6,7-dimethoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-4-yl)phenol 

Relevant academic research and scientific papers

New synthesis of (±)-cherylline and mono- and dimethyl ethers

The synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines is achieved via the ether rearrangement methodology. Subsequent reactions yielded cherylline and ether derivatives of amaryllidaceac alkaloids. Copyright