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CAS No.: | 1062580-52-2 |
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Name: | CIS-N-BENZYL-3-METHYLAMINO-4-METHYL-PIPERIDINE BIS-(HYDROCHLORIDE) |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C14H24Cl2N2 |
Molecular Weight: | 291.264 |
Synonyms: | (3R,4R)-N,4-Dimethyl-1-(phenylmethyl)-3-piperidi; |
Melting Point: | 249~251℃ |
PSA: | 15.27000 |
LogP: | 4.04920 |
N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride
Conditions | Yield |
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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 |
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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 |