1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.166667h; Inert atmosphere; | 89% |
3,4-dihydropapaverine
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With sodium (S)-prolinate-borane In tetrahydrofuran for 240h; Ambient temperature; | 78% |
With sodium tetrahydroborate for 19h; Ambient temperature; | 71% |
Tetrahydropapaverine
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol | 66% |
(3,4-Dimethoxyphenyl)acetic acid
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
(+/-)-Tetrahydropapaveroline hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide for 2.5h; Reflux; | 95.1% |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
formic acid ethyl ester
1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In ethanol for 40h; Bischler-Napieralski Reaction; Reflux; | 94% |
(3,4-Dimethoxyphenyl)acetic acid
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
(R)-tetrahydropapaverine hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.166667h; Inert atmosphere; | 89% |
3,4-dihydropapaverine
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With sodium (S)-prolinate-borane In tetrahydrofuran for 240h; Ambient temperature; | 78% |
With sodium tetrahydroborate for 19h; Ambient temperature; | 71% |
Tetrahydropapaverine
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol | 66% |
(3,4-Dimethoxyphenyl)acetic acid
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
(+/-)-Tetrahydropapaveroline hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide for 2.5h; Reflux; | 95.1% |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
formic acid ethyl ester
1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In ethanol for 40h; Bischler-Napieralski Reaction; Reflux; | 94% |
(3,4-Dimethoxyphenyl)acetic acid
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
(R)-tetrahydropapaverine hydrochloride
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
mesitylene-2-carboxylic acid chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | 83% |
formaldehyd
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline
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
Glyoxilic acid
Conditions | Yield |
---|---|
for 1h; Heating; | 80% |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
1,7-heptanediol dipropenoate
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 76% |
hexamethylene glycol diacrylate
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 67% |
1,6-hexanediol diacrylate
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 60% |
diethyleneglycol(diacrylate)
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 57% |
pentamethylene 1,5-diacrylate
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 51% |
2-propenoic acid 1,3-propanediyl ester
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 50% |
1,4-Butanediol diacrylate
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 48% |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
3-methyl-1,5-pentanediol dipropenoate
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 38% |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
Acrylic acid 2-[4-(2-acryloyloxy-ethyl)-phenyl]-ethyl ester
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
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 35% |
hydrogenchloride
diethyl acetal
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
A
(8R,13aR)-2,3,10,11-tetramethoxy-8-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
hydrogenchloride
Dimethoxymethane
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
hydrogenchloride
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
A
methylene chloride
Conditions | Yield |
---|---|
at 170 - 175℃; |
1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
(+/-)-Xylopinin-trans-methiodid
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
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
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
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
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
pseudopalmatine
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
(+/-)-O-methylcorytenchirine
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
7,14-dehydroxylopinine
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 |
Product Name: Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-,hydrochloride (1:1) (CAS NO.6429-04-5)
Molecular Formula: C20H25NO4.HCl
Molecular Weight: 379.8814g/mol
Mol File: 6429-04-5.mol
EINECS: 229-213-9
Boiling point: 475.8 °C at 760 mmHg
Flash Point: 202.7 °C
Enthalpy of Vaporization: 73.93 kJ/mol
Vapour Pressure: 3.23E-09 mmHg at 25°C
H-Bond Donor: 2
H-Bond Acceptor: 5
Structure Descriptors of Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-,hydrochloride (1:1) (CAS NO.6429-04-5):
IUPAC Name: 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
Canonical SMILES: COC1=C(C=C(C=C1)CC2C3=CC(=C(C=C3CCN2)OC)OC)OC.Cl
InChI: InChI=1S/C20H25NO4.ClH/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;1H
InChIKey: VMPLLPIDRGXFTQ-UHFFFAOYSA-N
Classification Code: Drug / Therapeutic Agent
Safety Information of Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-,hydrochloride (1:1) (CAS NO.6429-04-5):
Hazard Codes: T
Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-,hydrochloride (1:1) , its CAS NO. is 6429-04-5, the synonyms are 1,2,3,4-Tetrahydro-6,7-dimethoxy-1-veratryl-isoquinoline hydrochloride ; Papaverine, 1,2,3,4-tetrahydro-, hydrochloride ; Tetrahydropapaverine hydrochloride ; 1-(3,4-Dimethoxybenzyl)-1,2,3,4-tetrahydro-6,7-
dimethoxyisoquinolinium chloride ; Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-veratryl-, hydrochloride .
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