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formaldehyd
formic acid
rac-nornicotine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: formaldehyd; formic acid; rac-nornicotine In water at 85℃; for 20h; Stage #2: With sodium hydroxide In water pH=13; | 99.1% |
formaldehyd
3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With formic acid In water at 80℃; for 18h; | 98% |
D-nicotine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium tert-butylate at 80℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere; | 96.5% |
With sodium hydride In o-xylene for 15h; Reflux; | 66.8% |
With sodium hydride In o-xylene for 15h; Reflux; | 66.8% |
nicotin
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With 15-crown-5; sodium t-butanolate at 80℃; for 2h; Reagent/catalyst; Inert atmosphere; | 94.7% |
With sodium hydride In xylene for 6h; Heating; | 66% |
With potassium hydride In xylene for 1h; Product distribution; Heating; other reagent, solvent, reaction time; |
Conditions | Yield |
---|---|
With sodium cyanoborohydride In acetonitrile | 91% |
With formic acid at 30℃; Reagent/catalyst; | 91% |
Stage #1: formaldehyd; rac-nornicotine With polymer-bound trimethyl ammonium cyanoborohydride In water for 4h; Stage #2: With Amberlyst 15 In dichloromethane for 1h; Stage #3: With ammonia In methanol for 2h; | 88% |
ethyl N-methyl-N-<4-chloro-4-(3-pyridyl)butnyl>carbamate
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With sulfuric acid for 5h; Heating; further reagent; | 90% |
N-methylmyosmine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen In methanol at 20℃; under 7500.75 Torr; Autoclave; | 90% |
1:1 complex of 1,1,6,6-tetraphenyl-hexa-2,4-diyne 1,6-diol and nicotine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
In acetone | 86% |
(RS) 1-methyl-2-(3'-pyridyl)pyrrolidine-2-carbaldehyde
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With sodium hydroxide at 50℃; for 16h; | 80% |
methyl 2-(pyridin-3-yl)pyrrolidine-1-carboxylate
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; | 77% |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: 4-methylamino-1-(3-pyridyl)butanone hydrochloride In water at -5℃; for 5h; pH=8; Stage #2: With sodium tetrahydroborate In ethanol; water at -5 - 15℃; for 2h; Reagent/catalyst; Solvent; pH-value; | 72% |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol; water at -5 - 15℃; for 2h; Reagent/catalyst; Temperature; Solvent; | 72% |
1-methyl-3-nicotinoyl-2-pyrrolidone
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: 1-methyl-3-nicotinoyl-2-pyrrolidone With hydrogenchloride at 135℃; for 40h; Stage #2: With sodium tetrahydroborate; sodium hydroxide for 1.5h; pH=8; Concentration; Reagent/catalyst; Time; Temperature; Cooling with ice; | 71% |
3-Bromopyridine
N-methylsuccinimide
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: 3-Bromopyridine With n-butyllithium In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: N-methylsuccinimide In diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h; Inert atmosphere; | 65% |
C12H18N2Si
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran Reflux; | 60% |
methylamine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium carbonate In water at 110℃; for 2h; Inert atmosphere; Microwave irradiation; Green chemistry; | 50% |
(1R,2S,5S)-2-Isopropyl-5-methylcyclohexyl 2-(pyridin-3-yl)pyrrolidine-1-carboxylate
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; | 47% |
methylamine
4-Oxo-1-(3-pyridyl)-1-butanone
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: methylamine; 4-Oxo-1-(3-pyridyl)-1-butanone With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; dichloromethane at -78 - 20℃; Stage #2: With Amberlyst 15 In tetrahydrofuran; dichloromethane at 20℃; for 1h; Stage #3: With triethylamine In dichloromethane at 20℃; for 1h; | 46% |
nicotirine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With palladium on activated charcoal; charcoal catalyst Hydrogenation; |
tetrachloromethane
1-methyl-2-(3-pyridyl)-3-pyrroline
ethylene glycol
A
nicotirine
B
3-(1-methyl-pyrrolidin-2-yl)-pyridine
1-methyl-2-(3-pyridyl)-3-pyrroline
A
nicotirine
B
3-(1-methyl-pyrrolidin-2-yl)-pyridine
4-methylamino-1-[3]pyridyl-butan-1-ol
A
methyl-(4-pyridin-3-yl-but-3-enyl)-amine
B
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With phosphorus pentoxide; xylene |
Pseudooxynicotine
A
4-methylamino-1-[3]pyridyl-butan-1-ol
B
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water pH 9.0; |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; acetic acid at 25℃; Yield given; |
rac-nornicotine
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
ESCHWEILER-method; Yield given; |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With tetrahydrofuran; lithium aluminium tetrahydride |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide at 100℃; im Rohr; Behandeln des Reaktionsprodukts mit Alkalilauge und folgend Destillieren mit Wasserdampf; |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With water at 200℃; |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With sodium hypobromide Behandeln des entstandenen N-Brom-dihydrometanicotins in konz. Schwefelsaeure bei 20grad und Erhitzen der Loesung auf 100grad; |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
With aluminum oxide; silica gel; potassium carbonate; sodium percarbonate; sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine In chloroform column chromatography; | 95% |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
nicotin
Conditions | Yield |
---|---|
With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase for 16h; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 93% |
Stage #1: 3-(1-methyl-pyrrolidin-2-yl)-pyridine With O,O'-dibenzoyl-L-tartaric acid In ethanol Reflux; Stage #2: With ammonium hydroxide In water; toluene pH=9.8 - 10.4; | 70.8% |
Stage #1: 3-(1-methyl-pyrrolidin-2-yl)-pyridine In methanol Heating; Stage #2: With hydrogenchloride In methanol Further stages.; |
Conditions | Yield |
---|---|
for 0.00416667h; microvawe irradiation; | 92% |
3-(1-methyl-pyrrolidin-2-yl)-pyridine
cotinine
Conditions | Yield |
---|---|
With Hg(II)-EDTA In dichloromethane for 17h; Heating; pH 8.0; | 88% |
With ethylenediaminetetraacetic acid; mercury(II) diacetate; acetic acid for 2h; steam-bath; further reagent; | 70% |
With iodosylbenzene; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride In dichloromethane Mechanism; other catalysts; | 22% |
With iodosylbenzene; (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride In dichloromethane | 22% |
With ethylenediaminetetraacetic acid; mercury(II) diacetate |
S-tert-butyl O-ethyl carbonodithioate
3-(1-methyl-pyrrolidin-2-yl)-pyridine
2-(tert-butyl)-5-(1-methylpyrrolidin-2-yl)pyridine
Conditions | Yield |
---|---|
With dilauryl peroxide; camphor-10-sulfonic acid In 1,2-dichloro-ethane at 85℃; for 1h; Sealed tube; | 83% |
bis(pinacol)diborane
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 3-(1-methyl-pyrrolidin-2-yl)-pyridine In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere; | 82% |
triisopropylsilyl trifluoromethanesulfonate
di-tert-butylmagnesium
3-(1-methyl-pyrrolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
Stage #1: triisopropylsilyl trifluoromethanesulfonate; 3-(1-methyl-pyrrolidin-2-yl)-pyridine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: di-tert-butylmagnesium In 1,4-dioxane; diethyl ether; dichloromethane at -85℃; for 16h; Inert atmosphere; | 81% |
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