N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 0 - 5℃; pH=3 - 4; | 94% |
With hydrogenchloride In n-heptane; isopropyl alcohol at 20℃; for 0.666667h; Reflux; | 60% |
1-benzyl-4-methyl-piperidin-3-one
methylamine
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-benzyl-4-methyl-piperidin-3-one; methylamine With titanium tetrachloride; triethylamine In tetrahydrofuran at 20℃; for 4h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 25℃; Stage #3: With hydrogenchloride In ethanol | 85% |
1-benzyl-4-methyl-piperidin-3-one
methylamine acetate
A
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-benzyl-4-methyl-piperidin-3-one; methylamine acetate With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-3,5-di-tert-butyl-4-methoxyphenyl-(6,6’-dimethoxybiphenyl-2,2’-diyl)-bis(diphenylphosphine); hydrogen In dichloromethane; isopropyl alcohol at 70℃; under 37503.8 Torr; for 18h; Stage #2: With hydrogenchloride In dichloromethane; water; isopropyl alcohol Overall yield = 86%; Overall yield = 498 mg; enantioselective reaction; | A n/a B 74% |
(1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine
A
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; acetone for 1h; Inert atmosphere; Overall yield = 498 mg; |
1-benzyl-4-methyl-piperidin-3-one
A
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ethanol / 5 h / 20 °C / Inert atmosphere 2: hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-diMe-PipPhos / isopropyl alcohol / 18 h / 20 °C / 37503.8 Torr / Glovebox; Inert atmosphere 3: hydrogenchloride / acetone; diethyl ether / 1 h / Inert atmosphere View Scheme |
A
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-diMe-PipPhos / isopropyl alcohol / 18 h / 20 °C / 37503.8 Torr / Glovebox; Inert atmosphere 2: hydrogenchloride / acetone; diethyl ether / 1 h / Inert atmosphere View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2.83 h / 0 °C / Reflux 2: hydrogenchloride / isopropyl alcohol; n-heptane / 0.67 h / 20 °C / Reflux View Scheme |
(1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-yl)carbamic acid methyl ester
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogen; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (R)-1-[(Sp)-2-(di-tert-butylphosphino)ferrocenyl]ethylbis(2-methylphenyl)phosphine / 2,2,2-trifluoroethanol / 6 h / 30 - 50 °C / 2625.26 Torr 2: lithium aluminium tetrahydride / tetrahydrofuran / 2.83 h / 0 °C / Reflux 3: hydrogenchloride / isopropyl alcohol; n-heptane / 0.67 h / 20 °C / Reflux View Scheme |
3-amino-4-methylpyridine
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dichloromethane; toluene / 10 h / 20 - 25 °C / Large scale 1.2: 70 - 80 °C / Large scale 1.3: 14 h / 10 °C / Large scale 2.1: hydrogenchloride / water; n-heptane / 70 - 75 °C / Large scale 2.2: 0 - 5 °C / Large scale 3.1: Di-p-toluoyl-L-tartaric acid / methanol / 1 h / 50 - 55 °C / Large scale 3.2: 2 h / pH 3 / Large scale View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water; n-heptane / 70 - 75 °C / Large scale 1.2: 0 - 5 °C / Large scale 2.1: Di-p-toluoyl-L-tartaric acid / methanol / 1 h / 50 - 55 °C / Large scale 2.2: 2 h / pH 3 / Large scale View Scheme |
1-benzyl-4-methyl-piperidin-3-one
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-benzyl-4-methyl-piperidin-3-one With Di-p-toluoyl-L-tartaric acid In methanol at 50 - 55℃; for 1h; Large scale; Stage #2: With hydrogenchloride In methanol; water for 2h; pH=3; Large scale; | 1.7 kg |
benzyl chloride
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dichloromethane; toluene / 10 h / 20 - 25 °C / Large scale 1.2: 70 - 80 °C / Large scale 1.3: 14 h / 10 °C / Large scale 2.1: hydrogenchloride / water; n-heptane / 70 - 75 °C / Large scale 2.2: 0 - 5 °C / Large scale 3.1: Di-p-toluoyl-L-tartaric acid / methanol / 1 h / 50 - 55 °C / Large scale 3.2: 2 h / pH 3 / Large scale View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine
Conditions | Yield |
---|---|
Stage #1: N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride; 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine With potassium carbonate In water at 98 - 102℃; for 10h; Stage #2: at 20 - 25℃; for 4h; | 93.6% |
With potassium carbonate In water at 90℃; Reagent/catalyst; Solvent; Temperature; | 89.5% |
With potassium carbonate In water for 10h; Reflux; | 82.3% |
Stage #1: N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride With potassium carbonate In water Large scale; Stage #2: 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine In water at 100℃; Large scale; | 4.72 kg |
4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7-p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In water; dimethyl sulfoxide at 107℃; for 9h; Temperature; Large scale; | 93% |
Stage #1: N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride With potassium carbonate In water Stage #2: 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine In water at 90 - 95℃; | 155 g |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide at 115 - 120℃; for 12h; | 82% |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
With potassium carbonate; p-toluenesulfonyl chloride; sodium hydroxide In water; acetone; acetonitrile at 0 - 95℃; for 1h; | 77% |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Stage #1: N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 0.166667h; Stage #2: 3,4,6-trichloro-1H-pyrazolo[3,4-d]pyrimidine In ethanol at 100℃; for 2h; | 24.9% |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
Conditions | Yield |
---|---|
With potassium carbonate In water for 24h; Reflux; | 0.48% |
With potassium carbonate In water at 90℃; | 145 g |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water Reagent/catalyst; Solvent; Reflux; | 280 g |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; water / 9 h / 107 °C / Large scale 2: sodium hydroxide; water / dimethyl sulfoxide / 1 h / 80 °C / Large scale 3: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 3 h / 61 °C / 760.05 Torr / Large scale 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 1 h / 49 °C / Large scale 5: water / 96 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water / 10 h / Reflux 2: acetic acid; 5%-palladium/activated carbon; triethylsilane / methanol / 0.17 h / 30 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / butan-1-ol / 0.17 h / 80 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: dichloromethane / -20 °C 4: water; ethanol / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: tetrahydrofuran / 45 °C 4: water; ethanol / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: tetrahydrofuran / 45 °C 4: water; ethanol / 0 °C View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; water / 9 h / 107 °C / Large scale 2: sodium hydroxide; water / dimethyl sulfoxide / 1 h / 80 °C / Large scale View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / water 1.2: 90 - 95 °C 2.1: potassium hydroxide; methanol / 40 - 45 °C View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; water / 9 h / 107 °C / Large scale 2: sodium hydroxide; water / dimethyl sulfoxide / 1 h / 80 °C / Large scale 3: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 3 h / 61 °C / 760.05 Torr / Large scale View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; water / 9 h / 107 °C / Large scale 2: sodium hydroxide; water / dimethyl sulfoxide / 1 h / 80 °C / Large scale 3: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 3 h / 61 °C / 760.05 Torr / Large scale 4: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 1 h / 49 °C / Large scale View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water / 90 °C 2: acetic acid; 20% palladium hydroxide-activated charcoal; hydrogen / water 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / butan-1-ol View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: dichloromethane / -20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: tetrahydrofuran / 45 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr 3: tetrahydrofuran / 45 °C View Scheme |
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / water / 24 h / Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 24 h View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / water / 10 h / Reflux 2: acetic acid; 5%-palladium/activated carbon; triethylsilane / methanol / 0.17 h / 30 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / water / 90 °C 2: acetic acid; 20% palladium hydroxide-activated charcoal; hydrogen / water View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / water / 90 °C 2: hydrogen; hydrogenchloride; palladium on carbon / water / 120 °C / 2068.65 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / water 1.2: 90 - 95 °C 2.1: potassium hydroxide; methanol / 40 - 45 °C 3.1: hydrogenchloride / water / 20 °C / pH 3.5 - 4.5 3.2: 45 - 50 °C View Scheme |
R20:Harmful by inhalation.
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