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CAS No. : | 885278-83-1 | MDL No. : | MFCD07371656 |
Formula : | C14H20N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 248.32 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; water at 20℃; | Step 1: 3,4,5-Trimethyl-piperazine-l-carboxylic acid benzyl ester Benzyl 3,5-dimethylpiperazine-l-carboxylate (1 eq, 2.04 mmol, 0.5 g) and formaldehyde (37% in H2O, 5eq, 10.07 mmol, 0.277 ml) are dissolved in MeOH (10 ml). After 10 mins at room temperature, acetic acid (5eq, 10.07 mmol, 0.576 ml) and sodium triacetoxyborohydride (5eq, 10.07 mmol , 2.13 g) are added and the reaction mixture stirred overnight. The reaction is quenched with 5M HCl (15 ml) and the solvent evaporated under vacuo. The residue is taken to pH 13 by addition of sodium hydroxide (4M) and extracted with EtOAc. This organic portion is washed with water and brine, dried over MgSθ4, filtered and concentrated in vacuo to afford the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanol; water / 20 °C 2.1: sodium tris(acetoxy)borohydride; acetic acid / methanol; water / 20 °C 2.2: pH 13 3.1: hydrogen / palladium on activated charcoal / ethanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: methanol; water / 20 °C 2.1: sodium tris(acetoxy)borohydride; acetic acid / methanol; water / 20 °C 2.2: pH 13 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In water for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane for 4h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C 3: 1,2-dichloro-ethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 4 h / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / Petroleum ether 2: potassium carbonate / Petroleum ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / Petroleum ether 2: potassium carbonate / Petroleum ether 3: Petroleum ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / Petroleum ether 2: potassium carbonate / Petroleum ether 3: Petroleum ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triethylamine / Petroleum ether 2: potassium carbonate / Petroleum ether 3: Petroleum ether 5: potassium cyanate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: triethylamine / Petroleum ether 2: potassium carbonate / Petroleum ether 3: Petroleum ether 5: potassium cyanate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In Petroleum ether | 15 Example 15 To a solution of (3S,5R)-benzyl 3,5-dimethylpiperazine-1-carboxylate (5.000 g, 20.14 mmol, 1 equiv.) in dichloromethane (50 mL) was added triethylamine (4.2 mL, 30.20 mmol, 1.5 equiv.) followed by 2-chloroacetyl chloride (1.76 mL, 22.15 mmol, 1.1 equiv.) drop-wise at 0° C. and the reaction mixture was stirred at 0° C. After 2 h the reaction solution was concentrated and purified by silica gel column chromatography (20-50% ethyl acetate in petroleum ether) to afford benzyl (3S,5R)-4-(2-chloroacetyl)-3,5-dimethylpiperazine-1-carboxylate (3.300 g, 10.16 mmol, 51% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.41-7.34 (m, 5H), 5.19 (s, 2H), 4.60 (m, 1H), 4.16-4.07 (m, 5H), 3.07 (br, s, 2H), 1.32 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With potassium carbonate | 16 Example 16 To a solution of (3R,5S)-benzyl 3,5-dimethylpiperazine-1-carboxylate (5.000 g, 20.140 mmol, 1 equiv.) and 1,3-dibromopropane (40.65 g, 201.35 mmol, 10 equiv.) in acetonitrile (50 mL) was added potassium carbonate (8.350 g, 60.410 mmol, 3 equiv.) and the reaction mixture was stirred at 100° C. After 12 h the reaction solution was diluted with ethyl acetate (100 mL), filtered and concentrated. The resulting crude material was purified y silica gel column chromatography (25-50% ethyl acetate in petroleum ether) to give benzyl (3R,5S)-4-(3-bromopropyl)-3,5-dimethylpiperazine-1-carboxylate (2.000 g, 5.630 mmol, 28% yield) as a colorless oil. MS (ESI) m/z 371.0 [M+1]+; 1H NMR (400 MHz, CDCl3) δ 7.39-7.30 (m, 5H), 5.13 (s, 2H), 3.96-3.91 (m, 2H), 3.39-3.36 (t, J=6.4 Hz, 2H), 2.91-2.87 (m, 2H), 2.62-2.54 (m, 4H), 1.97-1.90 (m, 2H), 1.10-1.09 (d, J=5.2 Hz, 6H). |