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CAS No. : | 149715-46-8 | MDL No. : | MFCD11113046 |
Formula : | C12H18N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PJMFGDYBTJEEDP-GFCCVEGCSA-N |
M.W : | 206.28 | Pubchem ID : | 7145274 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H312-H315-H319-H332-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 |
---|---|---|
56% | With hydrogen In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating; | |
17.85 g | With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 80℃; Inert atmosphere; | 3.4 (4) Synthesis of (R)-(4-benzyl-2-yl)methanol ((R)-(4-benzylpiperazin-2-yl)methanol, e5): In the formula, d: Take about 200mL of anhydrous THF (tetrahydrofuran) to a 500mL round bottom flask,Under ice water bath conditions,Add 12.35g (324.9mmol) LiAlH4 (lithium aluminum hydride) and stir for 5 minutes,After adding 20.00g (85.5mmol) e4 in batches,Under N2 protection, stir at room temperature for 30 minutes,Heat to reflux at 80°C for 3-6 hours.TLC detection (EA: methanol (MeOH) = 20:1 development) raw material disappeared,The reaction was quenched, filtered, and the mother liquor was extracted 3 times with dichloromethane,The amount of dichloromethane used for each time is 30 mL, the combined organic phase is washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent.17.85g of yellow liquid was obtained. |
17.85g | With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 80℃; Inert atmosphere; | 10 Preparation of compound e5 (e4→e5): Take about 200mL of anhydrous THF toIn a 500mL round bottom flask,Under ice water bath conditions,Add 12.35g (324.9mmol) LiAlH4 and stir for 5min,After adding 20.00g (85.5mmol) e4 in batches,Under N2 protection, stir at room temperature for 30 minutes,Heat to reflux at 80°C for 3-6h (preferably 4h).TLC detection (developed by EA: MeOH = 20:1) disappeared, the reaction was quenched, filtered, the mother liquor was extracted three times with 30 mL of dichloromethane, the combined organic phase was washed with sat.NaCl, dried with anhyd.Na2SO4, and the solvent was evaporated under reduced pressure ,17.85g of yellow liquid was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With lithium aluminium tetrahydride In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 78 percent / TEA 2: 82 percent / LiAlH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent 2: 100 percent / H2 / Pd-C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 93 percent 2: 100 percent / H2 / Pd-C 3: 71 percent / TEA / CHCl3 4: 68 percent / TBAF / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 93 percent 2: 100 percent / H2 / Pd-C 3: 71 percent / TEA / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 56 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: 96 percent / acetonitrile / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 56 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: 96 percent / acetonitrile / 0.5 h / Ambient temperature 3: 1.) 1,1'-carbonyldiimidazole, 3.) LiOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 56 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: 96 percent / acetonitrile / 0.5 h / Ambient temperature 3: 1.) 1,1'-carbonyldiimidazole, 3.) LiOH 4: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) N-methylmorpholine / 1.) dichloromethane, -68 deg C, 2.5 h, 2.) dichloromethane, -20 deg C, 45 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 56 percent / H2 / 5percent Pd/C / ethanol / 760 Torr 2: 96 percent / acetonitrile / 0.5 h / Ambient temperature 3: 1.) 1,1'-carbonyldiimidazole, 3.) LiOH 4: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) N-methylmorpholine / 1.) dichloromethane, -68 deg C, 2.5 h, 2.) dichloromethane, -20 deg C, 45 min 5: HCl, NaBH3CN, 3A molecular sieves / methanol / 18 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) SOCl2, 2.) aq. NH3 / 1.) methanol, RT, 2 h, 2.) methanol 2: 91 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 4.1.1. General procedure for the synthesis of acyl and sulfonyl amides General procedure: To a solution of the suitable amine (0.3 g, 1 eq) and Et3N (1.1 eq)in anhydrous CH2Cl2 (5 mL), at 0 C and under N2 atmosphere, the suitable acyl or sulfonyl chloride (0.7 eq for the synthesis of 12 a-d,1 eq for the synthesis of the other derivatives) in anhydrous CH2Cl2 (7 mL) was slowly added dropwise. The reaction was left stirring at RT for 2 h; for the synthesis of 12a-d the reaction was stopped when from TLC there was evidence for the formation of the productof double addition. The mixture was then washed twice with sat.aq. NaHCO3; after drying (Na2SO4), the solvent was removed under vacuum, and the residue was purified by flash chromatography. By this method the following compounds were obtained: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethanol / 3723.56 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethanol / 3723.56 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethanol / 3723.56 Torr 3: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / ethanol / 3723.56 Torr 3: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 4.1.1. General procedure for the synthesis of acyl and sulfonyl amides General procedure: To a solution of the suitable amine (0.3 g, 1 eq) and Et3N (1.1 eq)in anhydrous CH2Cl2 (5 mL), at 0 C and under N2 atmosphere, the suitable acyl or sulfonyl chloride (0.7 eq for the synthesis of 12 a-d,1 eq for the synthesis of the other derivatives) in anhydrous CH2Cl2 (7 mL) was slowly added dropwise. The reaction was left stirring at RT for 2 h; for the synthesis of 12a-d the reaction was stopped when from TLC there was evidence for the formation of the productof double addition. The mixture was then washed twice with sat.aq. NaHCO3; after drying (Na2SO4), the solvent was removed under vacuum, and the residue was purified by flash chromatography. By this method the following compounds were obtained: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 0.08 h / Cooling with ice 1.2: Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 - 80 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 0.08 h / Cooling with ice 1.2: Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: palladium(II) hydroxide; palladium on activated charcoal; acetic acid; hydrogen / methanol / 20 °C 3: isopropyl alcohol / 60 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: palladium(II) hydroxide; palladium on activated charcoal; acetic acid; hydrogen / methanol / 20 °C 3: isopropyl alcohol / 60 °C / Sealed tube 4: hydrogenchloride / 1,4-dioxane / 20 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.41% | With triethylamine In dichloromethane at 20℃; Cooling with ice; | 3.5 (5)(R)-tert-butyl4-benzyl-2-(hydroxymethyl)piperazine-1-carboxylate ((R)-tert-butyl4-benzyl-2-(hydroxymethyl)piperazine-1-carboxylate , The synthesis of e6): E in the formula: take 17.85g (87.0mmol) e5 to a 250mL round bottom flask,Add 75mL of dichloromethane to dissolve, stir under ice bath,Add 9.67g (95.7mmol) of triethylamine,Drop (Boc)2O (di-tert-butyl dicarbonate) solution,20.86g (95.7mmol) dissolved in 75mL dichloromethane,After the addition is complete, react at room temperature overnight.TLC detection (PE:EA=5:1 development) the raw material disappeared, add 100mL of water, extract twice with dichloromethane,The amount of dichloromethane used for each time is 100 mL, and the combined organic phase is washed with saturated brine and dried with anhydrous sodium sulfate.The solvent was removed by distillation under reduced pressure, and the crude weight was 25.00 g.Purified by column chromatography (PE:EA=10:1→2:1),16.60 g of light yellow liquid was obtained, and the yield was 62.41%. |
62.41% | With triethylamine In dichloromethane at 20℃; Cooling with ice; | 10 Preparation of compound e6 (e5→e6): Take 17.85g (87.0mmol) e5 to 250mL round bottom flask,Add 75mL of dichloromethane to dissolve, stir under ice bath conditions, add 9.67g (95.7mmol) of triethylamine,(Boc)2O (di-tert-butyl dicarbonate) solution was added dropwise, 20.86g (95.7mmol) dissolved in 75mL dichloromethane,After the addition is complete, react at room temperature overnight.TLC detection (PE:EA=5:1 development) raw material disappeared, add 100mL water, extract twice with 100mL dichloromethane, the combined organic phase was washed with sat.NaCl water, dried with anhyd.Na2SO4, evaporated under reduced pressure to remove the solvent, the crude weight was 25.00 g. Purified by column chromatography (PE:EA=10:1→2:1), 16.60 g of pale yellow liquid was obtained with a yield of 62.41% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 0.08 h / Cooling with ice 1.2: Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 - 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: palladium on activated charcoal; palladium(II) hydroxide; acetic acid; hydrogen / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: palladium on activated charcoal; palladium(II) hydroxide; acetic acid; hydrogen / methanol / 20 °C 3: ethanol / 60 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 20 °C / Cooling with ice 2: palladium on activated charcoal; palladium(II) hydroxide; acetic acid; hydrogen / methanol / 20 °C 3: ethanol / 60 °C / Sealed tube 4: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C / Sealed tube |
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