1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
In ethanol Heating; | 97% |
1-methyl-4-phenyl-2(1H)-pyridone
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; titanium(III) chloride In tetrahydrofuran at 0℃; | 97% |
4-phenyl-N-methylpyridinium iodide
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | A 92% B 0.5% |
sodium tetrahydroborate
4-phenyl-N-methylpyridinium iodide
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
In methanol to a soln. of pyridinium iodide in methanol cooling in an ice bath NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30min at room temp.; | A 92% B 0.5% |
In water to a soln. of pyridinium iodide in water (cooled in an ice bath) NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30 min at room temp.; extn. with ether, extract dried over Na2SO4 and evapd. to dryness; chromy. on silica gel column with CH2Cl2; elem. anal.; | A 60% B 22% |
4-phenyl-N-methylpyridinium iodide
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With tetrahydroxydiboron; potassium tert-butylate; water In methanol at 60℃; for 8h; Reagent/catalyst; Solvent; Inert atmosphere; | 91% |
With sodium tetrahydroborate In methanol | |
Multi-step reaction with 2 steps 1: 0.5 percent / sodium borohydride / methanol 2: 97 percent / ethanol / Heating View Scheme |
1-methyl-4-phenyl-piperidin-4-ol
acetonitrile
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
B
N-(1-methyl-4-phenyl-[4]piperidyl)-acetamide
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; for 24h; | A n/a B 86% |
1-methyl-4-phenyl-piperidin-4-ol
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
B
N-(1-methyl-4-phenyl-[4]piperidyl)-acetamide
Conditions | Yield |
---|---|
With sulfuric acid In acetonitrile at 20℃; for 24h; | A n/a B 86% |
1-methyl-4-phenyl-piperidin-4-ol
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With sulfuric acid; sodium cyanide In acetic acid for 6h; | 64% |
With hydrogenchloride | |
With hydrogen bromide; acetic acid | |
With hydrogenchloride for 4h; Heating; Yield given; |
sodium tetrahydroborate
1-methyl-3-phenyl-1-pyridinium iodide
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
In water to a soln. of pyridinium iodide in water (cooled in an ice bath) NaBH4 was added with stirring, mixt. stirred for 15 min at 0°C and 30 min at room temp.; extd. with ether, extract dried over Na2SO4 and evapd. to dryness; chromy. on silica gel column with CH2Cl2; elem. anal.; | A 60% B 22% |
3,6-dimethyl-6-phenyl-1,3-oxazinane
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
B
1-methyl-4-phenyl-piperidin-4-ol
Conditions | Yield |
---|---|
With hydrogenchloride |
1-methyl-4-phenyl-piperidin-4-ol
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
B
4-amino-1-methyl-4-phenylpiperidine
Conditions | Yield |
---|---|
With potassium hydroxide; sodium cyanide 1.) acetic acid / H2SO4; 2.) ethanol, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given; |
1-methyl-4-phenyl-2(1H)-pyridone
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; deuteromethanol 1.) THF, 0 deg C, 2 h, 2.) -78 deg C; Multistep reaction; |
methylamine hydrochloride
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With formaldehyd; sulfuric acid |
tetrachloromethane
thionyl chloride
A
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
B
benzonitrile
1-Methyl-4-piperidone
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 10percent HCl / 4 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: benzene 2: acetic acid; aqueous hydrobromic acid View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: acetic acid; aqueous hydrobromic acid View Scheme | |
Multi-step reaction with 2 steps 1: benzene 2: concentrated aqueous hydrochloric acid View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: concentrated aqueous hydrochloric acid View Scheme |
phenyllithium
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 10percent HCl / 4 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: acetic acid; aqueous hydrobromic acid View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether 2: concentrated aqueous hydrochloric acid View Scheme |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene 2: acetic acid; aqueous hydrobromic acid View Scheme | |
Multi-step reaction with 2 steps 1: benzene 2: concentrated aqueous hydrochloric acid View Scheme |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With potassium carbonate |
p-phenylpyridine
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetone / 12 h / 90 °C / Inert atmosphere 2: water; tetrahydroxydiboron; potassium tert-butylate / methanol / 8 h / 60 °C / Inert atmosphere View Scheme |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide
Conditions | Yield |
---|---|
With dihydrogen peroxide In ethanol at 50℃; for 8h; | 94% |
With dihydrogen peroxide; palladium on activated charcoal In ethanol; dichloromethane a) 60 deg C, 20 h, b) 60 deg C, 3 h; | 46% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With potassium permanganate In water; acetonitrile at 20 - 30℃; for 1.5h; | 76% |
Multi-step reaction with 2 steps 1: 65 percent / potassium permanganate / acetonitrile; H2O / 20 °C 2: 76 percent / potassium permanganate / H2O; acetonitrile / 2 h / 30 °C View Scheme |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
α-bromoacetophenone
1-methyl-1-(2-oxo-2-phenylethyl)-4-phenyl-1,2,3,6-tetrahydropyridinium bromide
Conditions | Yield |
---|---|
In benzene at 20℃; for 72h; | 75% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Diethyl 2-bromomalonate
1-di(ethoxycarbonyl)methyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; Reflux; Inert atmosphere; | 70% |
In tetrahydrofuran for 3h; Reflux; Inert atmosphere; |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1-methyl-4-phenyl-1,2,5,6-tetrahydropyridin-2-one
Conditions | Yield |
---|---|
With potassium permanganate In water; acetonitrile at 20℃; | 65% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
chloroacetic acid ethyl ester
Conditions | Yield |
---|---|
In benzene at 20℃; for 72h; | 62% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
diiodomethane
3-methyl-6-phenyl-3-azabicyclo[4.1.0]heptane
Conditions | Yield |
---|---|
With diethylzinc In dichloromethane; toluene at 20℃; for 18h; Simmons-Smith reaction; | 57% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1-(N-formyl-N-methyl)amino-3-phenylpropan-2-one
Conditions | Yield |
---|---|
With potassium permanganate In acetonitrile at 50℃; for 1h; | 53% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
p-phenylpyridine
Conditions | Yield |
---|---|
With manganese(IV) oxide In toluene for 3h; Heating; | 45% |
With manganese(IV) oxide In toluene for 3h; Heating; | 45% |
With aluminum oxide; palladium/alumina; nitrobenzene at 130℃; | |
Multi-step reaction with 2 steps 1: 22 percent / aq. NaOH; MnO2 / benzene / 1.5 h / 20 - 40 °C 2: 10 percent / aq. KMnO4 / acetonitrile / 1.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 36.5 percent / aq. MnO2 / benzene / 2 h / 20 °C 2: 10 percent / aq. KMnO4 / acetonitrile / 1.5 h / 20 °C View Scheme |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
nitromethane
Conditions | Yield |
---|---|
With potassium permanganate In chloroform for 2.5h; Ambient temperature; | 40% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
malononitrile
3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine
Conditions | Yield |
---|---|
With manganese(IV) oxide In benzene at 20℃; for 2h; | 36.5% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
4-nitro-aniline
A
1-methyl-4-phenyl-1,2,5,6-tetrahydropyridin-2-one
Conditions | Yield |
---|---|
With potassium permanganate In acetonitrile at 20℃; for 2h; | A 2% B 33% |
formaldehyd
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With manganese(IV) oxide; sulfuric acid for 7h; Prins reaction; Heating; | 31% |
With manganese(IV) oxide; sulfuric acid for 7h; Heating; | 31% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
acetone
Conditions | Yield |
---|---|
With potassium permanganate for 1.16667h; Ambient temperature; | A 30% B 12% |
formaldehyd
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydropyridine
Conditions | Yield |
---|---|
With manganese(IV) oxide; sodium hydroxide In benzene at 20 - 40℃; for 1.5h; | 22% |
With sulfuric acid Prins reaction; |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
aniline yellow
Conditions | Yield |
---|---|
With potassium permanganate In acetonitrile at 20℃; for 2h; | 20% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
3-(N-methylamino)propiophenone
Conditions | Yield |
---|---|
With potassium permanganate In acetonitrile at 20 - 60℃; for 26h; | 20% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
4-bromo-aniline
Conditions | Yield |
---|---|
With potassium permanganate In acetonitrile at 20℃; for 2h; | 17% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
acetophenone
Conditions | Yield |
---|---|
With potassium permanganate for 1.16667h; Ambient temperature; | 7% |
2-Acetylthiophene
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
Conditions | Yield |
---|---|
With potassium permanganate for 1.16667h; Ambient temperature; | 6% |
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1-methyl-4-phenyl-piperidin-4-ol
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid Erwaermen des Reaktionsprodukts in Wasser; |
1. | ipr-mus TDLo:30 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 293 (2000),336. |
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