Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 12h; | 82% |
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol under 7600 - 11400 Torr; for 1.5h; | 75% |
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr; | 81% |
With hydrogenchloride; zinc In ethanol; water at 40 - 60℃; for 3h; | 67.08% |
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C 2.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C 2.2: 2 h / -20 °C View Scheme |
3-methoxy-4-benzyloxy-ω-nitrostyrolene
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; iron(III) chloride; platinum In water for 4h; | 76% |
2-methoxy-4-(2-nitroethyl)phenol
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With hydrogenchloride; zinc In water; ethyl acetate at 50 - 70℃; for 3h; Stage #2: With hydrogenchloride In methanol at -20℃; for 2h; | 72% |
Stage #1: 2-methoxy-4-(2-nitroethyl)phenol With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; Stage #2: With hydrogenchloride In water | 31% |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 2: 85 percent / AcONa. Ac2O / 0.08 h / Heating 3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme | |
Multi-step reaction with 2 steps 1: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme |
1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / AcONa. Ac2O / 0.08 h / Heating 2: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 3: 85 percent / AcONa. Ac2O / 0.08 h / Heating 4: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme | |
Multi-step reaction with 3 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 3: 76 percent / conc. aq. HCl, FeCl3, H2 / Pt black / H2O / 4 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / dimethylformamide / 20 h / 130 °C 2: 82 percent / H2; HCl / Pd/C / ethanol / 12 h / 20 °C View Scheme |
2-(4-hydroxy-3-methoxyphenyl)acetamide
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(4-hydroxy-3-methoxyphenyl)acetamide With borane-THF In tetrahydrofuran at 0℃; for 8h; Reflux; Stage #2: With hydrogenchloride In water for 3h; Reflux; | 54.2 g |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: methanol; methylamine / 2 h / 50 °C 2.1: sodium tetrahydroborate / 1,4-dioxane; ethanol / 20 °C 3.1: hydrogenchloride; zinc / ethyl acetate; water / 3 h / 50 - 70 °C 3.2: 2 h / -20 °C View Scheme | |
Multi-step reaction with 3 steps 1: ethylenediamine / 4 h / Reflux 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 - 20 °C 3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C View Scheme |
3,4-dimethylphenylacetic acid
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
2-[4-(dimethylamino)phenyl]acetic acid
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere; | 99% |
bis(trichloromethyl) carbonate
3-Methoxytyramine hydrochloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
Stage #1: 3-Methoxytyramine hydrochloride With 1H-imidazole In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #3: bis(trichloromethyl) carbonate In toluene at 20 - 100℃; for 1.5h; Inert atmosphere; | 98% |
3-Methoxytyramine hydrochloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere; | 97% |
4-benzyloxy-3-methoxyphenylacetic acid
3-Methoxytyramine hydrochloride
2-[4-(benzyloxy)-3-methoxyphenyl]-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With triethanolamine; benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 15.25h; | 92% |
3-Methoxytyramine hydrochloride
acetic anhydride
N-acetyl-3-O-methyldopamine
Conditions | Yield |
---|---|
With potassium carbonate; triethylamine In methanol; chloroform | 91% |
With triethylamine In dichloromethane at 20℃; for 0.5h; | 87% |
(3,4-Dimethoxyphenyl)acetic acid
3-Methoxytyramine hydrochloride
2-(3,4-dimethoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]acetamide
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 91% |
o-methylmandelic acid
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; | 82% |
carbon dioxide
triisopropylsilyl trifluoromethanesulfonate
3-Methoxytyramine hydrochloride
C19H33NO4Si
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; 3-Methoxytyramine hydrochloride In dichloromethane at -78℃; for 1h; Stage #2: triisopropylsilyl trifluoromethanesulfonate at -78 - 20℃; | 78% |
With triethylamine In dichloromethane at -78℃; | 78% |
3-Methoxytyramine hydrochloride
benzaldehyde
6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol
Conditions | Yield |
---|---|
Stage #1: 3-Methoxytyramine hydrochloride; benzaldehyde With magnesium sulphate; triethylamine In methanol for 3h; Reflux; Stage #2: With trifluoroacetic acid In ethyl acetate for 1h; Reflux; Stage #3: With sodium hydrogencarbonate | 74% |
3-Methoxytyramine hydrochloride
trimethyl orthoformate
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide
Conditions | Yield |
---|---|
for 2h; Heating; | 71% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 71% |
formaldehyd
3-Methoxytyramine hydrochloride
1,2,3,4-tetrahydro-6-methoxy-7-isoquinolinol hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride at 70℃; for 1h; Pictet-Spengler isoquinoline synthesis; | 70% |
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 3h; | 70% |
Conditions | Yield |
---|---|
Stage #1: 3-Methoxytyramine hydrochloride With hydrogen bromide for 6h; Reflux; Stage #2: With hydrogenchloride In water | 69.81% |
3-Methoxytyramine hydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 69% |
formic acid
3-Methoxytyramine hydrochloride
N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide
Conditions | Yield |
---|---|
Stage #1: formic acid With acetic anhydride at 55℃; for 2h; Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 75℃; for 16h; Further stages.; | 66% |
Stage #1: formic acid With acetic anhydride at 0 - 55℃; for 2h; Stage #2: 3-Methoxytyramine hydrochloride In tetrahydrofuran at 0 - 75℃; for 18h; |
di-tert-butyl dicarbonate
3-Methoxytyramine hydrochloride
tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 24h; | 59% |
With sodium hydrogencarbonate; triethylamine; citric acid In water; ethyl acetate | |
With triethylamine In dichloromethane at 20℃; for 18h; | 4.59 g |
Conditions | Yield |
---|---|
Stage #1: 3-Methoxytyramine hydrochloride; acetaldehyde With hydrogenchloride In water at 100℃; for 24h; Pressure tube; Stage #2: With sodium hydrogencarbonate In water | 55% |
3-Methoxytyramine hydrochloride
acetaldehyde
Isosalsoline hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 24h; Sealed tube; | 55% |
3-Methoxytyramine hydrochloride
nonanoic acid N-hydroxysuccinimide ester
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate for 12h; | 46% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; 3-Methoxytyramine hydrochloride With hydrogenchloride In water at 50℃; for 6h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 17h; | 41.6% |
This chemical is called 5-(2-Aminoethyl)guaiacol hydrochloride, and its systematic name is 2-(4-hydroxy-3-methoxyphenyl)ethanaminium chloride. With the molecular formula of C9H13NO2.ClH, its CAS registry number of this chemical is 1477-68-5. It's often used as intermediate for dopamine. Additionally, this chemcial should be stored at the temperature of -20 °C.
Other characteristics of the 5-(2-Aminoethyl)guaiacol hydrochloride can be summarised as followings: (1)ACD/LogP: 0.43; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 18.46 Å2; (7)Flash Point: 138 °C; (8)Enthalpy of Vaporization: 56.66 kJ/mol; (9)Boiling Point: 304.5 °C at 760 mmHg; (10)Vapour Pressure: 0.000484 mmHg at 25°C.
Production method of this chemical: The 5-(2-Aminoethyl)guaiacol hydrochloride could be obtained by the reactant of 4-benzyloxy-3-methoxy-b-nitro-styrene. This reaction needs the reagents of conc. aq. HCl, FeCl3, H2, and the catalyst of Pt black. The yield is 76 %. In addition, this reaction should be taken for 4 hours.
Uses of this chemical: The 5-(2-Aminoethyl)guaiacol hydrochloride could react with nonanoic acid 2,5-dioxo-pyrrolidin-1-yl ester, and obtain the N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]nonanamide. This reaction needs the reagent of Et3N, and the solvent of ethyl acetate. The yield is 46 %. In addition, this reaction should be taken for 12 hours.
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1.SMILES: [Cl-].Oc1ccc(cc1OC)CC[NH3+]
2.InChI: InChI=1/C9H13NO2.ClH/c1-12-9-6-7(4-5-10)2-3-8(9)11;/h2-3,6,11H,4-5,10H2,1H3;1H
3.InChIKey: AWRIOTVUTPLWLF-UHFFFAOYAN
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