6429-04-5

Basic information

• Product Name: Tetrahydropapaverine hydrochloride
• Synonyms: 1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDETETRAHYDROPAPAVERINE HYDROCHLORIDE;tetrahydropapaverine crystalline*hydrochloride;TETRAHYDROALKALI HYDROCHLORIDE;TETRAHYDROPAPAVERINE HCL;1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride;Tetrahydropapaverine hydrochloride;1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINEHYDROCHLORIDETETRAHYDROPAPAVERINEHYDROCHLORIDE;6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-dihydroisoquinolineHydrochloride
• CAS NO: 6429-04-5
• Molecular Formula: C₂₀H₂₅NO₄*ClH
• Molecular Weight: 379.8814
• EINECS: 229-213-9
• Product Categories: Inhibitors
• Mol File: 6429-04-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 216.0 to 220.0 °C
• Boiling Point: 475.8 °C at 760 mmHg
• Flash Point: 202.7 °C
• Appearance: White crystal powder
• Density: 1.12g/cm3
• Vapor Pressure: 3.23E-09mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: Tetrahydropapaverine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydropapaverine hydrochloride(6429-04-5)
• EPA Substance Registry System: Tetrahydropapaverine hydrochloride(6429-04-5)

Safety Data

• Hazard Codes: T,Xn
• Statements: 22
• Safety Statements: 36
• RTECS: NX5070700
• Hazardous Substances Data: 6429-04-5(Hazardous Substances Data)

Usage

Uses

Tetrahydropapaverine hydrochloride is an organic amine compound that can be used as atracuramide intermediate.

Biological Activity

Tetrahydropapaverine (Norlaudanosine), a TIQs, is an analogue of Salsolinol and Tetrahydropapaveroline, and has neurotoxic effects on dopamine neurons.

InChI:InChI=1/C20H25NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-6,10-12,16,21H,7-9H2,1-4H3/t16-/m0/s1

Synthetic route

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride (5884-22-0) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.166667h; Inert atmosphere;	89%

3,4-dihydropapaverine (6957-27-3) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With sodium (S)-prolinate-borane In tetrahydrofuran for 240h; Ambient temperature;	78%
With sodium tetrahydroborate for 19h; Ambient temperature;	71%

Tetrahydropapaverine (13074-31-2) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With hydrogenchloride In ethanol	66%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / 2 h / 190 - 210 °C 2: phosphoryl chloride / toluene / 3 h / Heating 3: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1 h / 180 °C 2: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide (139-76-4) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride / toluene / 3 h / Heating 2: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + palladium/barium sulfate → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / 2 h / 190 - 210 °C 2: phosphoryl chloride / toluene / 3 h / Heating 3: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1 h / 180 °C 2: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (+/-)-Tetrahydropapaveroline hydrobromide (16659-88-4)

Conditions	Yield
With hydrogen bromide for 2.5h; Reflux;	95.1%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + formic acid ethyl ester (109-94-4) → 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde (50722-30-0)

Conditions	Yield
With potassium carbonate In ethanol for 40h; Bischler-Napieralski Reaction; Reflux;	94%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 1-(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(3,4-dimethoxyphenyl)ethanone

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 17h;	89%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (R)-tetrahydropapaverine hydrochloride (54417-53-7)

Conditions	Yield
With N-acetyl-D-leucine; (R)-N-acetylphenylalanin In water; toluene; acetonitrile at 4 - 70℃; for 24.92h; Reagent/catalyst;	83.25%

formaldehyd (50-00-0) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline (523-02-4, 4216-86-8, 6872-27-1, 13407-95-9)

Conditions	Yield
In ethanol; water at 20℃; for 8h;	80%
With acetic acid at 100℃; for 0.5h; Pictet-Spengler Synthesis;	73%
In water Cyclization; Heating;
In water for 30h; Heating;	8.2 g

1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride (5884-22-0) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.166667h; Inert atmosphere;	89%

3,4-dihydropapaverine (6957-27-3) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With sodium (S)-prolinate-borane In tetrahydrofuran for 240h; Ambient temperature;	78%
With sodium tetrahydroborate for 19h; Ambient temperature;	71%

Tetrahydropapaverine (13074-31-2) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
With hydrogenchloride In ethanol	66%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / 2 h / 190 - 210 °C 2: phosphoryl chloride / toluene / 3 h / Heating 3: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1 h / 180 °C 2: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide (139-76-4) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride / toluene / 3 h / Heating 2: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + palladium/barium sulfate → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / 2 h / 190 - 210 °C 2: phosphoryl chloride / toluene / 3 h / Heating 3: 71 percent / sodium borohydride / 19 h / Ambient temperature View Scheme

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1 h / 180 °C 2: trichlorophosphate / acetonitrile / 1 h / Reflux; Inert atmosphere 3: sodium tetrahydroborate; methanol / 0.17 h / 0 - 20 °C / Inert atmosphere View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (+/-)-Tetrahydropapaveroline hydrobromide (16659-88-4)

Conditions	Yield
With hydrogen bromide for 2.5h; Reflux;	95.1%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + formic acid ethyl ester (109-94-4) → 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde (50722-30-0)

Conditions	Yield
With potassium carbonate In ethanol for 40h; Bischler-Napieralski Reaction; Reflux;	94%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 1-(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-(3,4-dimethoxyphenyl)ethanone

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 17h;	89%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (R)-tetrahydropapaverine hydrochloride (54417-53-7)

Conditions	Yield
With N-acetyl-D-leucine; (R)-N-acetylphenylalanin In water; toluene; acetonitrile at 4 - 70℃; for 24.92h; Reagent/catalyst;	83.25%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + mesitylene-2-carboxylic acid chloride (938-18-1) → (1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)(mesityl)methanone

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	83%

formaldehyd (50-00-0) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline (523-02-4, 4216-86-8, 6872-27-1, 13407-95-9)

Conditions	Yield
In ethanol; water at 20℃; for 8h;	80%
With acetic acid at 100℃; for 0.5h; Pictet-Spengler Synthesis;	73%
In water Cyclization; Heating;
In water for 30h; Heating;	8.2 g

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + Glyoxilic acid (298-12-4) → 2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-8-carboxylic acid

Conditions	Yield
for 1h; Heating;	80%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + 1,7-heptanediol dipropenoate (61804-12-4) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 7-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-heptyl ester; compound with oxalic acid (81165-43-7)

Conditions	Yield
In benzene for 48h; Heating;	76%

hexamethylene glycol diacrylate (13048-33-4) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 6-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-hexyl ester; compound with oxalic acid (81182-08-3)

Conditions	Yield
In benzene for 48h; Heating;	67%

1,6-hexanediol diacrylate (10526-04-2) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 8-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-octyl ester; compound with oxalic acid (81165-44-8)

Conditions	Yield
In benzene for 48h; Heating;	60%

diethyleneglycol(diacrylate) (4074-88-8) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-(2-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethoxy)-ethyl ester; compound with oxalic acid (81165-45-9)

Conditions	Yield
In benzene for 48h; Heating;	57%

pentamethylene 1,5-diacrylate (36840-85-4) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate (64228-78-0, 64493-10-3, 83285-74-9, 96687-52-4, 96687-53-5, 110817-20-4)

Conditions	Yield
In benzene for 48h; Heating;	51%

2-propenoic acid 1,3-propanediyl ester (24493-53-6) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 3-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-propyl ester; compound with oxalic acid (81165-42-6)

Conditions	Yield
In benzene for 48h; Heating;	50%

1,4-Butanediol diacrylate (1070-70-8) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 4-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-butyl ester; compound with oxalic acid (81182-07-2)

Conditions	Yield
In benzene for 48h; Heating;	48%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + 3-methyl-1,5-pentanediol dipropenoate (64194-22-5) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 5-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-3-methyl-pentyl ester; compound with oxalic acid (81165-48-2)

Conditions	Yield
In benzene for 48h; Heating;	38%

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) + Acrylic acid 2-[4-(2-acryloyloxy-ethyl)-phenyl]-ethyl ester (36431-64-8) → 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 2-[4-(2-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-ethyl)-phenyl]-ethyl ester; compound with oxalic acid (81165-47-1)

Conditions	Yield
In benzene for 48h; Heating;	35%

hydrogenchloride (7647-01-0) + diethyl acetal (105-57-7) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (8R,13aR)-2,3,10,11-tetramethoxy-8-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline (6899-65-6) + β-coralydine

hydrogenchloride (7647-01-0) + Dimethoxymethane (109-87-5) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → norcoralydine

hydrogenchloride (7647-01-0) + 1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → methylene chloride (74-87-3) + Py-tetrahydro-papaveroline

Conditions	Yield
at 170 - 175℃;

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (+/-)-Xylopinin-trans-methiodid (52194-51-1, 52194-52-2, 52194-53-3, 52438-48-9, 57129-74-5, 62860-05-3, 62860-06-4, 65025-46-9, 120052-37-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.2 g / H2O / 30 h / Heating 2: 122 mg / acetone; CHCl3 / 1 h / 20 °C View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (+/-)-2,3,10,11-tetrademethylpseudotetrahydropalmatine hydrobromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.2 g / H2O / 30 h / Heating 2: 1.85 g / HBr / 7 h / Heating View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 2,3,10,11-tetramethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolinium; iodide

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.2 g / H2O / 30 h / Heating 2: acetone; CHCl3 / 1 h / 20 °C View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → C22H25(2)H3NO4(1+)*I(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.2 g / H2O / 30 h / Heating 2: 71 mg / acetone; CHCl3 / 2.5 h / 20 °C View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → C22H25(2)H3NO4(1+)*I(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.2 g / H2O / 30 h / Heating 2: 290 mg / acetone; CHCl3 / 2.5 h / 20 °C View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → pseudopalmatine (19716-66-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: H2O / Heating 2.1: 55 percent / mCPBA / CHCl3 / 20 °C 3.1: TFAA / CH2Cl2 / -30 - 20 °C 3.2: NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → (+/-)-O-methylcorytenchirine (6899-65-6, 7058-95-9, 57030-06-5, 58116-07-7, 58116-10-2, 58116-12-4, 79297-66-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: H2O / Heating 2.1: 55 percent / mCPBA / CHCl3 / 20 °C 3.1: TFAA / CH2Cl2 / -30 - 20 °C 3.2: 49 percent / NaOAc / CH2Cl2; H2O / 0.5 h / 20 °C 4.1: 80 percent / methylmagnesium iodide / diethyl ether / 2 h / Heating View Scheme

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride (6429-04-5) → 7,14-dehydroxylopinine (332951-52-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O / Heating 2: 55 percent / mCPBA / CHCl3 / 20 °C 3: 50 percent Spectr. / acetyl chloride / 2 h / 25 °C View Scheme

Upstream product

• 5884-22-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3.4-dihydroisoquinoline hydrochloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 13074-31-2 Tetrahydropapaverine 
• 6957-27-3 3,4-dihydropapaverine 
• 139-76-4 N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 

Downstream Products

• 81182-07-2 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 4-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-butyl ester; compound with oxalic acid 
• 81165-42-6 3-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid 3-{3-[1-(3,4-dimethoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]-propionyloxy}-propyl ester; compound with oxalic acid 
• 50722-30-0 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde 
• 141109-12-8 (R)-tetrahydropapaverine N-acetyl-L-leucine salt 
• 50720-57-5 (S)-(-)-norlaudanosine (-)-N-acetyl-L-leucine 
• 54417-53-7 (R)-tetrahydropapaverine hydrochloride 
• 2688-77-9 (S)-laudanosine 
• 85-63-2 (R)-laudanosine 
• 1232653-32-5 (+/-)-N,N-digeranyltetrahydropapaveroline trifluoroacetate 
• 16659-88-4 (+/-)-Tetrahydropapaveroline hydrobromide 
• 876290-45-8 (R)-tetrahydropapaverine-N-acetyl-D-leucine salt 
• 13074-31-2 Tetrahydropapaverine 
• 53094-01-2 6-hydroxy-7-methoxy-1-(3',4'-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 106073-63-6 5-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol 

Relevant articles and documents

Total synthesis of 8-epi-javaberine A and javaberine A

The total synthesis of berberine alkaloid javaberine A was examined. The B/C ring of berberine was successfully constructed by sequential Bischler-Napieralski cyclization-reduction protocols, and final demethylation afforded both javaberine A and its epimer.

Asymmetric Reduction of Cyclic Imines with Chiral Sodium Acyloxyborohydrides

Asymmetric reduction of prochiral cyclic imines with chiral sodium acyloxyborohydrides (5a-i), which are easily prepared by the reaction of NaBH4 with various N-acyl α-amino-acids, has been investigated.Of these new reducing agents, triacyloxyborohydrides (5c-f), derived from NaBH4 (1 equiv.) and (S)-N-acylproline (3 equiv.), were found to reduce 3,4-dihydropapaverine (2) in tetrahydrofuran to (S)-norlaudanosine (3) hydrochloride in 60percent optical yield.The N-benzyloxycarbonyl derivative (5c) could be isolated as a powder and characterized.The effect of solvents on this asymmetric reduction has been examined by the use of the isolated reagent (5c); halogenated alkane solvents such as CH2Cl2 or CHCl2CH3 gave a better optical yield of compound (3) (79percent e.e.).The reagent (5c) also reduced other cyclic imines (6a-c) and (8) to the corresponding alkaloids (7a-c) and (9) in excellent optical yields (70-86percent e.e.), providing an effective route to the asymmetric synthesis of these alkaloids.A possible reaction path for this reduction is also presented.