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[ CAS No. 116797-02-5 ]

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Chemical Structure| 116797-02-5
Chemical Structure| 116797-02-5
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Product Details of [ 116797-02-5 ]

CAS No. :116797-02-5 MDL No. :MFCD03274731
Formula : C11H22N2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :182.31 g/mol Pubchem ID :-
Synonyms :

Safety of [ 116797-02-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 116797-02-5 ]

  • Downstream synthetic route of [ 116797-02-5 ]

[ 116797-02-5 ] Synthesis Path-Downstream   1~15

  • 1
  • N-[(benzyloxy)carbonyl]-4-methyl-[1,4']bipiperidine [ No CAS ]
  • [ 116797-02-5 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogen In ethanol at 20℃; for 2h;
  • 2
  • [ 626-58-4 ]
  • [ 116797-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C 2: 64 percent / H2 / Pd/C / ethanol / 2 h / 20 °C
  • 3
  • [ 19099-93-5 ]
  • [ 116797-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 51 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C 2: 64 percent / H2 / Pd/C / ethanol / 2 h / 20 °C
  • 4
  • [ 40064-34-4 ]
  • [ 116797-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 90 percent / Na2CO3 / dioxane; H2O / 2 h / 20 °C 2: 51 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 20 °C 3: 64 percent / H2 / Pd/C / ethanol / 2 h / 20 °C
  • 5
  • [ 116797-02-5 ]
  • [ 911370-07-5 ]
  • [ 911370-51-9 ]
YieldReaction ConditionsOperation in experiment
51% With triethylamine In dichloromethane at -20℃; 51 Example 51; 4-chloro-8-r2,6-difluorophenylV2-('4-methyl-1.4'-bipiperidin-l'-vDρyridor2,3-To the compound 4-chloro~8-(2,6-difluorophenyl)-2-(methylsulfinyl)pyrido[2,3-0C overnight. Filtration followed by concentration, the crude was purified with flash chromatography to afford the title compound (0.904 g, 51%). LC-MS m/z 474 (M+Η)+.
51% With triethylamine In dichloromethane at -20℃; 163.163a Example 163; 3-[8-r2.6-difiuorophenylV2-('4-methyl-l,4'-bipiperidm-r-yl)-7-oxo-7.8- dihydropyrido[2n3-'l-methylethyl)benzamide163a) 4-chloro-8-f2,6-difluorophenylV2-('4-methyl-1.4'-bipiperidin-r-vϖpyrido("2,3-To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(methylsulfinyl)ρyrido[233-0C overnight. Filtration followed by concentration, the crude was purified with flash chromatography to afford the title compound (0.904 g, 51 %). LC-MS m/z 474 (M+Η)+.
51% With triethylamine In dichloromethane at -20℃; 51 To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(methylsulfmyl)pyrido[2,3-J]pyrimidin-7(8H)-one (1.39 g, 3.9 mmol) in dichloromethane (80 mL) were added A- methyl-l,4'-bipiperidine (0.75 g, 5.85 mol) and triethylamine (1.03 mL, 11.7 mmol). The mixture was stirred at about -200C overnight. Filtration followed by concentration, the crude was purified with flash chromatography to afford the title compound (0.904 g, 51%). LC-MS m/z 474 (M+η)+.
51% With triethylamine In dichloromethane at -20℃; 163.163a To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(methylsulfnyl)pyrido[2,3- (i]pyrimidin-7(8H)-one (1.39 g, 3.9 mmol) in dichloromethane (80 mL) were added 4-methyl- 1 ,4'-bipiperidine (0.75 g, 5.85 mol) and triethylamine (1.03 mL, 11.7 mmol). The mixture was stirred at -200C overnight. Filtration followed by concentration, the crude was purified with flash chromatography to afford the title compound (0.904 g, 51%). LC-MS m/z 474 (M+η)+.

  • 6
  • [ 116797-02-5 ]
  • [ 911693-62-4 ]
  • 3-[8-(2,6-difluorophenyl)-2-(4-methyl-1,4'-bipiperidin-1'-yl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(1-methylethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 20℃; 70 Example 70; 3-f8-(2,6-difluorophenylV2-(4-methyl-1.4'-bipiperidin-r-ylV7-oxo-5,6J,8- tetrahvdropyrimido[4,5-
70% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 20℃; 70 To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfnyl)-7-oxo- 5,6,7,8-tetrahydropyrimido[4,5-3 (2mL) were added 4-methyl-l,4'-bipiperidine (40 mg, 0.22 mmol) and JV,jV-diisopropylethylamine (0.1 mL, 0.5 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (31 mg, 70%). LC-MS m/z 618 (M + H)+; 1H- NMR (MeOD) δ 1.00 (d, 3 H), 1.22 (m, 2 H), 1.27 (d, 6 H), 1.38 (m, 3 H), 1.68 (d, 2H), 1.81 (d, 2 H), 2.19 (t, 2 H), 2.30 (s, 3 H), 2.50 (t, 1 H), 2.71 (t, 2H), 2.93 (d, 2 H), 4.11 (s, 2 H), 4.23 (m, 1 H), 4.45 (m, 2 H), 7.16 (t, 2 H), 7.46 (d, 1 H), 7.50 (m, 1 H), 7.68 (s, 1 H), 7.85 (d, I H).
  • 8
  • [ 116797-02-5 ]
  • 3-azido-4-(prop-2-yn-1-yloxy)benzaldehyde [ No CAS ]
  • 1′-(3-azido-4-(prop-2-yn-1-yloxy)benzyl)-4-methyl-1,4′-bipiperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.0378 g With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 28h; 1.X Synthesis of 1′-(3-azido-4-(prop-2-yn-1-yloxy)benzyl)-4-methyl-1,4′-bipiperidine A mixture of 3-methyl-1,4′-bipiperidine (0.0865 g, 0.048 mmol), the 3-azido-4-(prop-2-yn-1-yloxy)benzaldehyde (above), CH2Cl2 (2 mL), AcOH (0.027 mL, 0.47 mmol) and NaBH(OAc)3 (0.1425 g, 0.67 mmol) was stirred at room temperature for 28 h. The reaction was then quenched by saturated NaHCO3 solution (20 ml) at 0° C. and the generated bi-phase solution was extracted with CH2Cl2 (4×15 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The flash chromatography on silica gel (1:9 Methanol:CH2Cl2) provided the desired product as a yellow gel (0.0378 g, 22% over three steps). 1H NMR (400 MHz, CDCl3) δ 7.10-6.87 (m, 3H), 4.72 (d, J=2.4 Hz, 2H), 3.38 (s, 2H), 3.03-2.85 (m, 4H), 2.51 (t, J=2.4 Hz, 1H), 2.41 (s, 1H), 2.24 (d, J=11.8 Hz, 2H), 1.93 (td, J=11.9, 2.2 Hz, 2H), 1.84 (d, J=9.9 Hz, 2H), 1.61 (m, 5H), 1.37 (s, 2H), 0.91 (d, J=5.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 148.5, 133.0, 128.9, 125.9, 120.9, 114.1, 78.0, 76.1, 62.7, 61.9, 56.9, 53.1, 49.4, 33.8, 30.8, 27.5, 21.7; MS (ESI) m/z 368.2 (100%, [M+H]+).
  • 9
  • [ 116797-02-5 ]
  • benzyl (3-(chlorosulfonyl)-4-methoxyphenyl)carbamate [ No CAS ]
  • Benzyl (4-methoxy-3-((4-methyl-[1,4'-bipiperidin]-1'-yl)sulfonyl)phenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.3318 g With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 21h; 1.XI A mixture of 4-methyl-1,4'-bipiperidine (1.2090 g, 6.64 mmol), benzyl (3-(chlorosulfonyl)-4-methoxyphenyl)carbamate (above), N, N-diisopropyl ethylamine (3 mL, 18.19 mmol), and CH2Cl2 (15 mL) were stirred at room temperature for 21 h. The solution was then diluted with CH2Cl2 (20 mL) and washed by saturated NaHCO3 solution (35 mL) and brine (35 mL) The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (1:19 Methanol:CH2Cl2) to afford the desired product as a white solid (2.3318 g, 77% three steps). mp 124-127° C.; 1H NMR (400 MHz, CDCl3) δ 7.80 (s, br, 1H), 7.67 (d, J=2.8 Hz, 1H), 7.43-7.30 (m, 4H), 6.95 (d, J=9.0 Hz, 1H), 6.89 (s, 1H), 5.18 (s, 2H), 3.89 (s, J=3.4 Hz, 1H), 3.87 (s, 3H), 2.79 (d, J=11.5 Hz, 2H), 2.66-2.53 (m, 2H), 2.29 (tt, J=11.6, 3.5 Hz, 1H), 2.19-2.06 (m, 2H), 1.96-1.72 (m, 3H), 1.68-1.48 (m, 4H), 1.31 (ddt, J=14.5, 6.7, 3.7 Hz, 1H), 1.25-1.10 (m, 2H), 0.89 (d, J=6.3 Hz, 3H); 13C NMR (100 MHz, CDCl3) 153.6, 153.0, 135.9, 130.8, 128.6, 128.4, 128.3, 126.9, 125.1, 122.2, 113.2, 67.2, 61.8, 56.4, 49.5, 45.9, 34.6, 31.1, 27.9, 21.9; MS (ESI) m/z 502.2 (100%, [M+H]+). 4-methoxy-3-((4-methyl-[1,4'-bipiperidin]-1'-yl)sulfonyl)aniline:
2.3318 g With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 21h;
  • 10
  • [ 116797-02-5 ]
  • [ 19551-16-7 ]
  • 2,7-bis((4-methyl-[1,4'-bipiperidin]-1'-yl)sulfonyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; 1.II 2,7-bis((4-methyl-[1,4′-bipiperidin]-1′-yl)sulfonyl)naphthalene: A mixture of amine (1.0 mmol), sulfonyl chloride (1.1 mmol), N,N-diisopropyl ethylamine (1.5 mmol), and CH2Cl2 (5 mL) was stirred at room temperature overnight. The reaction solution was then poured into saturated NaHCO3 solution (20 ml) and extracted by CH2Cl2 (3*20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified either through flash chromatography on silica gel with a MeOH:CH2Cl2 (or MeOH:EtOAc) mixture as eluent or by recrystallization from a mixture of CH2Cl2 and hexane to provide the sulfonamides.This compound was obtained as a white solid (92%) through flash chromatography (1:19 MeOH:CH2Cl2) after the reaction of 4-methyl-1,4′-bipiperidine (0.39 mmol) with naphthalene-2,7-disulfonyl dichloride (0.15 mmol) in CH2C12 (2.5 mL) in the presence of N, N-diisopropyl ethylamine (0.52 mmol). mp 265-268° C.; NMR (400 MHz, CDCl3) δ 8.42 (s, 2H), 8.04 (d, J=8.7 Hz, 2H), 7.89 (dd, J=8.6, 1.7 Hz, 2H), 3.92 (d, J=12.3 Hz, 4H), 2.75 (d, J=11.7 Hz, 4H), 2.32 (td, J=12.1, 2.4 Hz, 4H), 2.25-1.99 (m, 6H), 1.84 (d, J=11.5 Hz, 4H), 1.72-1.51 (m, 8H), 1.37-1.21 (m, 2H), 1.21-1.07 (m, 4H), 0.86 (d, J=6.3 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 136.0, 135.5, 131.3, 129.7, 129.2, 125.8, 61.4, 49.5, 46.2, 34.5, 31.0, 27.4, 21.8; MS (ESI) m/z 617.3 (100%, [M+H]+)
  • 11
  • [ 116797-02-5 ]
  • [ 98-09-9 ]
  • 4-methyl-1'-(phenylsulfonyl)-1,4'-bipiperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; 1.II General Procedure for the Preparation of Sulfonamides from Sulfonyl Chlorides and Amines General procedure: A mixture of amine (1.0 mmol), sulfonyl chloride (1.1 mmol), N,N-diisopropyl ethylamine (1.5 mmol), and CH2Cl2 (5 mL) was stirred at room temperature overnight. The reaction solution was then poured into saturated NaHCO3 solution (20 ml) and extracted by CH2Cl2 (3*20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified either through flash chromatography on silica gel with a MeOH:CH2Cl2 (or MeOH:EtOAc) mixture as eluent or by recrystallization from a mixture of CH2Cl2 and hexane to provide the sulfonamides. 4-methyl-1'-(phenylsulfonyl)-1,4'-bipiperidine: This compound was obtained as a pale yellow solid (92%) through flash chromatography (1:9 MeOH:EtOAc) after the reaction between 4-methyl-1,4'-bipiperidine and benzenesulfonyl chloride. mp 154-156° C.; 1H NMR (500 MHz, CDCl3) δ 7.77 (dd, J=8.3, 1.4 Hz, 2H), 7.65-7.58 (m, 1H), 7.54 (dd, J=8.4, 7.0 Hz, 2H), 3.87 (d, J=11.9 Hz, 2H), 2.80 (d, J=11.8 Hz, 2H), 2.26 (m, 3H), 2.14 (t, J=11.4 Hz, 2H), 1.86 (d, J=11.7 Hz, 2H), 1.72-1.59 (m, 4H), 1.40-1.28 (m, 1H), 1.23 (m, 2H), 0.91 (d, J=6.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 136.0, 132.7, 129.0, 127.6, 61.3, 49.1, 46.1, 33.9, 30.8, 26.9, 21.7; MS (ESI) m/z 323.2 (100%, [M+H]+).
92% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
  • 12
  • [ 116797-02-5 ]
  • [ 1679-64-7 ]
  • methyl 4-[(3-methyl-1,4'-bipiperidin-1'-yl)carbonyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: Monomethyl terephthalate With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-(4-methylpiperidin-1-yl)piperidine In N,N-dimethyl-formamide at 20℃; 22 Methyl 4-[(3-methyl-1,4'-bipiperidin-1'-yl)carbonyl]benzoate Example 22 Methyl 4-[(3-methyl-1,4'-bipiperidin-1'-yl)carbonyl]benzoate 2.7 g (15 mmol) of 4-(methoxycarbonyl)benzoic acid, 2.75 g (17.95 mmol) of HOBT, 3.44 g (17.95 mmol) of EDC and 7.82 ml (25 mmol) of N,N-diisopropylethylamine were dissolved in 60 ml of DMF, and the mixture was stirred at RT for 1 h. 3.0 g (16.45 mmol) of 4-(4-methylpiperidin-1-yl)piperidine were then added, and the mixture was stirred at RT overnight. The reaction mixture was allowed to stand at RT for 2 days. The mixture was poured into water and extracted with ethyl acetate. The organic phase was separated off, dried over magnesium sulphate and filtered, and the filtrate was concentrated. The residue was purified by preparative HPLC [Reprosil C18, 10 μm, 250 mm*40 mm (15% methanol/85% water (isocratic to 15 min) then gradient to 100% methanol) over a run time of 35 min]. After HPLC control, the product-containing fractions were combined and concentrated. The residue was dried under HV. This gave 1.7 g (32% of theory) of an oil. LC-MS [Method 1]: Rt=0.59 min; MS (ESIpos): m/z=345 (M+H)+ 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=0.82 (d, 3H), 0.71-0.94 (m, 1H), 1.28-1.86 (m, 10H), 1.98-2.14 (m, 1H), 2.65-2.84 (m, 4H), 2.93-3.06 (m, 1H), 3.42-3.55 (m, 1H), 3.87 (s, 3H), 4.43-4.97 (m, 1H), 7.46-7.58 (m, 2H), 7.96-8.06 (m, 2H).
  • 13
  • [ 116797-02-5 ]
  • [ 388118-89-6 ]
  • 7,8-dihydroxy-3-(4-methyl-[1,4-bipiperidinyl]-1'-carbonyl)-6-nitro-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.26g With potassium carbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 40℃; for 8h; 6 Example 6,Preparation of Compound 9 (7,8-dihydroxy-3-(4-methyl-[1,4-bipiperidinyl]-1'-carbonyl)-6-nitro-2H-chromen-2-one Preparation of In 50ml single neck flask was added 0.53g hydroxy substrate,Then 0.51 g of piperidine fragment 2 was added,Then add 20ml DMF,After stirring for 10 minutes,Add 1g of anhydrous potassium carbonate,After stirring for 10 minutes,Add 1.14g HATU,Warming to 40°C,Insulation reaction 8h.Cool to room temperaturefilter,The cake was washed first with 5ml DMF.Then wash with 5ml 1:1 hydrochloric acid.Finally washed with 5 ml of purified water,The resulting filter cake was air dried at 100°C for 1 hour.0.26 g of a pale yellow solid was obtained.
  • 14
  • [ 116797-02-5 ]
  • 7-hydroxy-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid [ No CAS ]
  • 7-hydroxy-8-methyl-3-(4-methyl-[1,4-bipiperidinyl]-1'-carbonyl)-6-nitrate-2H-benzopyran-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.30g With potassium carbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 40℃; for 8h; 5 Example 5 preparation of Compound 8 (7-Hydroxy-8-methyl-3-(4-methyl-[1,4-bipiperidinyl]-1'-carbonyl)-6-nitro-2H-benzopyran-2 -ketone In 50ml single neck flask was added 0.53g Methyl substrate,Then 0.51 g of piperidine fragment 2 was added,Then add 20ml DMF,After stirring for 10 minutes,Add 1g of anhydrous potassium carbonate,After stirring for 10 minutes,Add 1.14g HATU,Warming to 40°C,Insulation reaction 8h.Cool to room temperaturefilter,The cake was washed first with 5ml DMF.Then wash with 5ml 1:1 hydrochloric acid.Finally washed with 5 ml of purified water,The resulting filter cake was air dried at 100°C for 1 hour.0.30 g of a pale yellow solid is obtained.
  • 15
  • [ 116797-02-5 ]
  • [ 98-58-8 ]
  • 1'-((4-bromophenyl)sulfonyl)-4-methyl-1,4'-bipiperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
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