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[ CAS No. 3703-76-2 ] {[proInfo.proName]}

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Chemical Structure| 3703-76-2
Chemical Structure| 3703-76-2
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Product Details of [ 3703-76-2 ]

CAS No. :3703-76-2 MDL No. :MFCD00866854
Formula : C20H24ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 329.86 Pubchem ID :-
Synonyms :

Safety of [ 3703-76-2 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 3703-76-2 ]

* 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.

  • Downstream synthetic route of [ 3703-76-2 ]

[ 3703-76-2 ] Synthesis Path-Downstream   1~19

YieldReaction ConditionsOperation in experiment
<2-Chlor-ethyl>-<phenyl-(4-chlor-phenyl)-methyl>-ether, 2 mol Piperidin, Benzol, 100grad;
  • 2
  • [ 119-56-2 ]
  • [ 3703-76-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / toluene / 5 h / Reflux 2: sodium carbonate / 14 h / 95 °C
  • 3
  • [ 110-89-4 ]
  • [ 5321-46-0 ]
  • [ 3703-76-2 ]
YieldReaction ConditionsOperation in experiment
80.7% With sodium carbonate at 95℃; for 14h; 1 The above 390g oil into 2000mL dry clean three reaction flask, to which was added anhydrous sodium carbonate150g, 180g (2.118mol) of piperidine, heating at 3 / min heating rate to 95 incubated for 14h;After the completion of the reaction, the obtained reaction product was distilled under reduced pressure to recover the piperidine, and the substrate after the piperidine was recovered was cooled to room temperatureTemperature, add 800mL of water to it, then add concentrated hydrochloric acid to adjust the pH value to 2, stir the layers and separate the water layer;The aqueous layer with a concentration of 42% of the caustic soda pH value to 9, with 1000mL ethyl acetate was extracted three times, the combined organicphase;The combined organic phases are dried over anhydrous sodium sulphate and concentrated by filtration to give a light brown oil.The structure of the obtained light brown oil was identified in the present invention and the result shows that the light brown is racemic chlorphenesTing.The present invention weighed racemic clorpsteretin, the result was 393.5g, the calculated yield was 87%;
  • 4
  • [ 3703-76-2 ]
  • [ 132301-89-4 ]
YieldReaction ConditionsOperation in experiment
With di-p-anisoyl-L-tartaric acid In ethanol at 60℃; for 2h; 1 To 1000mL dry clean three reaction flask, followed by the addition of racemic Clopidone 131.8g (0.4mol) and 300mL of ethanol, stir and dissolve, to which 200.8g (0.48mol) of the resolving agent L - (- ) - two pairs of methoxy benzoyl tartaric acid (from Zhejiang Dongyang Chemical Factory) to 4 / min heating rate of the system was heated to 60 insulation 2h;After the completion of the split, the system was naturally cooled double salt precipitation solid, suction filtration, the resulting double salt solid recrystallization with ethanol once, the white double salt.The above white double salt into 1000mL clean reaction flask, to which 400mL of deionized water was added, stirred, neutralized with sodium hydroxide to a pH of 9 to 10, the solution was white double salt solid dissolved completely; the resulting solution with Ethyl acetate extraction three times, the combined organic phase;The resulting organic phase was dried over anhydrous sodium sulfate and filtered to give a pale yellow oil.In the present invention, the above HPLC detection method is used, and the obtained levobisperidone is detected by HPLC analysis. As a resultShown in Figure 1, Figure 1 is obtained in Example 1 of the present invention levobisperidone HPLC profile, as can be seen from Figure 1, L-chlorineThe retention time of Pisidine is about 7.85min, the purity of Levocetirizol obtained in this example is 99.5%
  • 5
  • [ 3703-76-2 ]
  • [ 84627-04-3 ]
  • levocloperastine fendizoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.2% In water; acetone for 2h; Reflux; 1 To 500mL dry clean three reaction flask, followed by the addition of 50g (0.152mol) levopipeline, 53g(0.166mol) Fen to octanoic acid, 300mL of acetone and 50mL of water, stirred, warmed to reflux, the reaction was refluxed for 2h;After the reaction was completed, the reaction system was cooled to room temperature, the resulting reaction product was filtered, washed and dried to give a white solidBody products.
  • 6
  • [ 3703-76-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: Cloperastine With water-d2; lithium carbonate; triisopropylsilanethiol In 1-methyl-pyrrolidin-2-one at 20℃; Irradiation; Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one
  • 7
  • [ 3703-76-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With tritium oxide In 1-methyl-pyrrolidin-2-one at 20℃; Irradiation;
  • 8
  • [ 745783-97-5 ]
  • [ 3703-76-2 ]
  • [ 2413385-54-1 ]
YieldReaction ConditionsOperation in experiment
88% With 3,4,7,8-Tetramethyl-o-phenanthrolin; ferrous iodide; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;
  • 9
  • [ 3703-76-2 ]
  • [ 2247828-93-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
78% In dichloromethane at 70℃; for 3h; 62 Reference Example 62
1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxopropoxy]methyl]piperidinium Iodide 409 mg (1.24 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 443 mg (1.24 mmol) of 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethylpropane acid iodomethyl ester, and the reaction solution was condensed at 70° C. over 1 hour and then stirred at the same temperature for 2 hours. The residue was purified by silica gel column chromatography (2% methanol/chloroform) to obtain 668 mg (78%) of the title compound. 1H-NMR(CDCl3, δ):1.22(611, s), 1.34 (9H, s), 1.77-2.01 (6H, m), 3.25 (2H, d, J=7 Hz), 3.64-3.71 (2H, m), 3.98-3.99 (2H, m), 4.03-4.05 (2H, m), 4.15-4.16 (2H, m), 4.88(1H, br-s), 5.57 (1H, s), 5.59 (1H, d, J=9 Hz), 5.62 (1H, d, J=9 Hz), 7.26-7.36 (9H, m)
  • 10
  • [ 3703-76-2 ]
  • [ 2137597-06-7 ]
  • [ 2247829-65-6 ]
YieldReaction ConditionsOperation in experiment
85% In dichloromethane at 70℃; for 1h; 56 Reference Example 56
1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methyl-1-oxobutoxy]methyl]piperidinium Chloride 472 mg (1.43 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 200 mg (0.71 mmol) of 2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methylbutanoic acid chloromethyl ester, and the reaction solution was condensed at 70° C. over 1 hour and then stirred at the same temperature overnight. The residue was purified by silica gel column chromatography (2→10% methanol/chloroform) to obtain 367 mg (85%) of the title compound. 1H-NMR (CDCl3, δ):0.94 (3H, d, J=7 Hz), 0.97 (3H, d, J=7 Hz), 1.40 (9H, s), 1.77-1.99 (7H, m), 2.59(1H, br-s), 3.29-3.43 (2H, m), 3.65-3.76 (2H, m), 3.95-4.05 (4H, m), 4.16-4.24 (2H, m), 5.07(1H, br-s), 5.48(1H, s), 5.71-5.84 (2H, m), 7.25-7.35 (9H, m)
  • 11
  • [ 3703-76-2 ]
  • [ 2598024-08-7 ]
  • [ 2598025-54-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80 % ee With tris(pentafluorophenyl)borate; scandium tris(trifluoromethanesulfonate); 2,6-bis[(4S,6S)-sec-butyl-2-oxazolin-2-yl]pyridine In dichloromethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;
  • 12
  • [ 3703-76-2 ]
  • [ CAS Unavailable ]
  • [ 2677770-21-5 ]
YieldReaction ConditionsOperation in experiment
59% With bis(1,5-cyclooctadiene)nickel (0); Dimethyl(phenyl)phosphine In toluene at 70℃; for 18h; Schlenk technique; Sealed tube;
  • 13
  • [ 3703-76-2 ]
  • [ 73183-34-3 ]
  • [ 2662263-26-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine-4-carbonitrile; potassium phosphate; 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; Sealed tube;
  • 14
  • [ 3703-76-2 ]
  • [ 132301-89-4 ]
  • [ 132301-91-8 ]
YieldReaction ConditionsOperation in experiment
With C42H49O98S21(21-)*21Na(1+) In methanol; aq. phosphate buffer Resolution of racemate; Instrumentation for HPLC The enantiomeric separation was carried out on a Jasco-1500 series HPLC system comprising an isocratic pump,a Rheodyne injector with a fixed loop of 20 μl, and a UVdetector. Borwin software was used for data processing. Theanalysis was conducted under isocratic elution at ambienttemperature. Kromasil C8column (150 × 4.6 mm, 5 μm) wasused for the study. Methanol and 5 mM KH2PO4containing10 mM S-β-CD3 (3.696 g for 200 mL of aqueous phase)at pH 3 (adjusted with 10% OPA) in the ratio of 45:55 v/vwas used as the mobile phase for enantiomeric separation ofCP. The mobile phase was filtered through a 0.45 μm nylon filter and sonicated for 5 min before use. The flow rate wasmaintained at 1 ml/min, and the injection volume was 20 μl.Detection was carried out at 225 nm.
  • 15
  • [ 3703-76-2 ]
  • [ 2763620-86-4 ]
YieldReaction ConditionsOperation in experiment
With chlorotris(triphenylphosphine) rhodium (I); (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; deuterium gas In tetrahydrofuran at 20℃; for 12h; Irradiation; Sealed tube;
  • 16
  • [ 3703-76-2 ]
  • [ 2412606-40-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
62% R.50 1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropyl]amino]carbonyl]oxy]methyl]piperidinium chloride Reference Example 50 1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropyl]amino]carbonyl]oxy]methyl]piperidinium chloride 308 mg (0.93 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 262 mg (0.93 mmol) of N-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropyl]carbamic acid chloromethyl ester, and the reaction solution was condensed at 75° C. over 1 hour and then stirred at the same temperature overnight. The residue was purified by silica gel column chromatography (1→10% methanol/chloroform) to obtain 351 mg (62%) of the title compound. 1H-NMR (CDCl3, δ): 0.88 (3H, d, J=7 Hz), 1.42 (9H, s), 1.75-1.90 (7H, m), 2.97-3.18 (4H, m), 3.58-3.76 (4H, m), 3.90-3.92 (2H, m), 4.10-4.17 (2H, m), 5.23 (1H, br-s), 5.46-5.53 (3H, m), 7.25-7.35 (9H, m), 8.26 (1H, br-s)
  • 17
  • [ 3703-76-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
41% R.41 1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]propoxy]carbonyl]oxy]methyl]piperidinium chloride Reference Example 41 1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]propoxy]carbonyl]oxy]methyl]piperidinium chloride 680 mg (2.06 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 368 mg (1.37 mmol) of carbonic acid chloromethyl. 3-[[(1,1-dimethylethoxy)carbonyl]amino]propyl ester, and the reaction solution was condensed at 70'C over 1 hour and then stirred at the same temperature overnight. The residue was purified by silica gel column chromatography (2>10% methanol/chloroform) to obtain 335 mg (41%) of the title compound. 1H-NMR (CDCl3, δ): 1.42 (9H, s), 1.76-1.97 (8H, m), 3.22 (2H, q, J=7 Hz), 3.71-3.78 (2H, m), 3.93-4.05 (4H, m), 4.22-4.26 (4H, m), 4.71 (1H, br-s), 5.46 (1H, s), 5.82 (1H, d, J=12 Hz), 5.84 (1H, d, J=12 Hz), 7.24-7.36 (9H, m)
  • 18
  • [ 432037-37-1 ]
  • [ 3703-76-2 ]
  • [ 2412606-55-2 ]
YieldReaction ConditionsOperation in experiment
41% In dichloromethane at 70℃; 41 1-[2-[(4-chlorophenyl)phenylmethoxy]ethyl]-1-[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]propoxy]carbonyl]oxy]methyl]piperidinium chloride 680 mg (2.06 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 368 mg (1.37 mmol) of carbonic acid chloromethyl. 3-[[(1,1-dimethylethoxy)carbonyl]amino]propyl ester, and the reaction solution was condensed at 70′C over 1 hour and then stirred at the same temperature overnight. The residue was purified by silica gel column chromatography (2>10% methanol/chloroform) to obtain 335 mg (41%) of the title compound. 1H-NMR (CDCl3, δ): 1.42 (9H, s), 1.76-1.97 (8H, m), 3.22 (2H, q, J=7 Hz), 3.71-3.78 (2H, m), 3.93-4.05 (4H, m), 4.22-4.26 (4H, m), 4.71 (1H, br-s), 5.46 (1H, s), 5.82 (1H, d, J=12 Hz), 5.84 (1H, d, J=12 Hz), 7.24-7.36 (9H, m)
  • 19
  • [ 3703-76-2 ]
  • [ 2412606-40-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
62% In dichloromethane at 75℃; 50 1-[2-[(4-chlorophenyl)phenyl methoxy]ethyl]-1-[[[[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropyl]amino]carbonyl]oxy]methyl]piperidinium chloride 308 mg (0.93 mmol) of cloperastine was added at room temperature to a dichloromethane solution of 262 mg (0.93 mmol) of N-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropyl]carbamic acid chloromethyl ester, and the reaction solution was condensed at 75° C. over 1 hour and then stirred at the same temperature overnight. The residue was purified by silica gel column chromatography (1→10% methanol/chloroform) to obtain 351 mg (62%) of the title compound. (0309) 1H-NMR (CDCl3, δ): 0.88 (3H, d, J=7 Hz), 1.42 (9H, s), 1.75-1.90 (7H, m), 2.97-3.18 (4H, m), 3.58-3.76 (4H, m), 3.90-3.92 (2H, m), 4.10-4.17 (2H, m), 5.23 (1H, br-s), 5.46-5.53 (3H, m), 7.25-7.35 (9H, m), 8.26 (1H, br-s)
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[ 3703-76-2 ]

Chemical Structure| 14984-68-0

A318189[ 14984-68-0 ]

1-(2-((4-Chlorophenyl)(phenyl)methoxy)ethyl)piperidine hydrochloride

Reason: Free-salt