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[ CAS No. 82241-22-3 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 82241-22-3
Chemical Structure| 82241-22-3
Structure of 82241-22-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 82241-22-3 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 82241-22-3 ]

SDS

Product Details of [ 82241-22-3 ]

CAS No. :82241-22-3MDL No. :MFCD01935745
Formula :C14H17N3Boiling Point :-
Linear Structure Formula :-InChI Key :XYBLCORUTWKJOI-UHFFFAOYSA-N
M.W :227.30Pubchem ID :702318
Synonyms :

Computed Properties of [ 82241-22-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 82241-22-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 82241-22-3 ]

  • Downstream synthetic route of [ 82241-22-3 ]

[ 82241-22-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 4295-06-1 ]
  • [ 6091-62-9 ]
  • [ 82241-22-3 ]
  • 2
  • [ 82241-22-3 ]
  • [ 814-68-6 ]
  • 1-(4-(2-methylquinolin-4-yl)piperazin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With triethylamine; In dichloromethane; at 0 - 20℃; A solution of 2-methyl-4-(piperazin-1-yl)quinolone (455 mg, 2.0 mmol) in DCM (20 mL) was cooled to 0 C. To the solution was added acryloyl chloride (217 mg, 2.4 mmol) followed by triethylamine (243 mg, 2.4 mmol). The solution was allowed to warm to room temperature and stirred overnight. The solution was washed with brine and the crude product was purified via basic alumina chromatography (100% ethyl acetate) to afford the product in 26% yield as a yellow oil (145 mg).1H NMR (400MHz, CDCl3): d 7.90-8.05 (m, 2H), 7.58-7.70 (ddd, J = 8.4, 6.8, 1.5 Hz, 1H), 7.40-7.50 (ddd, J = 8.2, 6.8, 1.3 Hz, 1H), 6.68-6.76 (s, 1H), 6.56-6.67 (dd, J = 16.8, 10.5 Hz, 1H), 6.30-6.40 (dd, J = 16.8, 2.0 Hz, 1H), 5.70-5.80 (dd, J = 10.5, 2.0 Hz, 1H), 3.70-4.06 (d, J = 54.7 Hz, 4H), 3.10-3.30 (t, J = 5.0 Hz, 4H), 2.62-2.72 (s, 3H).13C NMR (100MHz, CDCl3): d 165.5, 159.4, 156.2, 149.2, 129.26, 129.24, 128.3, 127.3, 124.9, 123.0, 121.6, 109.8, 52.3, 51.9, 45.8, 42.0, 25.6. HRMS (+ESI): Calculated: 282.17 (C17H19N3O). Observed: 282.1597.
  • 3
  • [ 82241-22-3 ]
  • 2-methyl-4-(4-((4-(p-tolyl)pyridin-3-yl)methyl)piperazin-1-yl)quinoline [ No CAS ]
  • 4
  • [ 82241-22-3 ]
  • (3-((4-(2-methylquinolin-4-yl)piperazin-1-yl)methyl)pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate [ No CAS ]
  • 5
  • [ 3099-31-8 ]
  • [ 82241-22-3 ]
  • 2-methyl-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)quinoline [ No CAS ]
  • 6
  • [ 3185-73-7 ]
  • [ 82241-22-3 ]
  • [ 1420814-46-5 ]
YieldReaction ConditionsOperation in experiment
0.2973 g With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20℃; To a solution of triphosgene (0.099 g, 0.33 mmol, 0.33 eq) in CH2Cl2 (10 mL), was slowly added 4-hydroxybiphenyl (0.1702 g, 1 mmol, 1 eq) and N,N-diisopropylethylamine (DIEA) (176 muL, 0.130 g, 1 mmol, 1 eq) as a solution in THF (10 mL). The reaction was stirred at room temperature for 30 min to generate the intermediate chloroformate. In a separate flask containing CH2Cl2 (10 mL), 2-methyl-4- piperazinoquinoline (0.3410 g, 1.5 mmol, 1.5 eq) was mixed with DIEA (263 muL, 0.195 g, 1.5 mmol, 1.5 eq). The mixture was stirred for 5 min at room temperature and then dropped into the flask containing the chloroformate. The reaction mixture was stirred at room temperature for another 30 min and partitioned between CH2Cl2 (50 mL) and saturated NH4Cl (50 mL). The organic layer was washed one more time with saturated NH4Cl (30 mL), dried over MgSO4 and filtered. The solvent was removed by rotary evaporation and the product was purified by silica gel column chromatography (1:1 ethyl acetate/hexanes) to afford JMN4 (0.2973 g, 0.702 mmol, 70%).
  • 7
  • tert-butyl 4-(2-methylquinolin-4-yl)piperazine-1-carboxylate [ No CAS ]
  • [ 82241-22-3 ]
YieldReaction ConditionsOperation in experiment
69% Step B: 2-Methyl-4-piperazin-1-yl-quinolineTo te/f-butyl 4-(2-methyl-4-quinolyl)piperazine-1-carboxylate (4.382 g, 13.38 mmol) was added 40 ml of a 1 : 1 mixture of dichloromethane and trifluoroacetic acid. The mixture was stirred at room temperature for 15 minutes. The mixture was evaporated to dryness under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with 5% sodium bicarbonate solution and 3M NaOH was added until the aqueous phase remained basic. The phases were separated, the aqueous phase was extracted twice with dichloromethane, the combined organic phases were washed with saturated sodium carbonate solution, water, dried over magnesium sulfate and evaporated to dryness. 2.1 g of a solid were obtained (9.25 mmol, 69%). MS (APCI): m/z = 227.8 [M+1]+.
  • 8
  • [ 32748-41-7 ]
  • [ 82241-22-3 ]
  • [ 1370266-00-4 ]
YieldReaction ConditionsOperation in experiment
65% Step C: (£)-4-Hydroxy-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]pent-2-en-1-one (A-178) (£)-4-Hydroxypent-2-enoic acid (67 mg, 0.52 mmol) was dissolved in anhydrous DMF (2.5 ml), DCC (107.5, 0.52 mmol) and HOAt (106.7 mg, 0.79 mmol) were added and the mixture was stirred at room temperature for 15 minutes. 2-Methyl-4-piperazin-1-yl- quinoline (118.2 mg, 0.52 mmol) was added and stirring was continued for 90 minutes. The mixture was evaporated to dryness, taken up in a mixture of acetonitrile and methanol and filtered. The filtrate was evaporated to dryness again and purified by preparative HPLC (gradient of water containing 0.1 % TFA and acetonitrile). 1 10 mg were obtained (0.33 mmol, 65%). MS (ES): m/z = 326.1 [M+1]+.
  • 9
  • [ 32748-41-7 ]
  • [ 82241-22-3 ]
  • [ 1370266-01-5 ]
  • 10
  • [ 1871-67-6 ]
  • [ 82241-22-3 ]
  • [ 1370264-32-6 ]
YieldReaction ConditionsOperation in experiment
77% Example 17: Synthesis of (£)-1-[4-(2-methyl-4-quinolyl)piperazin-1-yl]oct-2-en-1-one (A- 14)(£)-Oct-2-enoic acid (71.1 mg, 0.5 mmol) was dissolved in dichloromethane (1 ml) and a 2M solution of oxalyl chloride in dichloromethane was added (0.3 ml, 0.6 mmol). The solution was stirred at room temperature for one hour after which a drop of DMF was added. Stirring was continued for another hour, the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane (1 ml), the resulting solution was added to a solution of [82241-22-3]2-methyl-4-piperazin-1-yl-quinoline (103 mg, 0.45 mmol) and triethylamine (90muIota, 0.64 mmol) in dichloromethane (1 ml). The resulting mixture was stirred at room temperature overnight, diluted with dichloromethane (1 ml), washed with water and 2M NaOH (2 ml each) and evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1 % ammonia and acetonitrile) to yield 121.3 mg of a solid (0.34 mmol, 77%).
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