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[ CAS No. 35857-66-0 ] {[proInfo.proName]}

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Chemical Structure| 35857-66-0
Chemical Structure| 35857-66-0
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Product Details of [ 35857-66-0 ]

CAS No. :35857-66-0 MDL No. :MFCD09878797
Formula : C9H7Cl3O Boiling Point : -
Linear Structure Formula :- InChI Key :ULARDXFALKMJAJ-UHFFFAOYSA-N
M.W : 237.51 Pubchem ID :12371341
Synonyms :

Calculated chemistry of [ 35857-66-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.26
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 3.6
Log Po/w (WLOGP) : 3.81
Log Po/w (MLOGP) : 3.51
Log Po/w (SILICOS-IT) : 4.29
Consensus Log Po/w : 3.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.72
Solubility : 0.0448 mg/ml ; 0.000189 mol/l
Class : Soluble
Log S (Ali) : -3.65
Solubility : 0.0537 mg/ml ; 0.000226 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00232 mg/ml ; 0.00000977 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.48

Safety of [ 35857-66-0 ]

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

Application In Synthesis of [ 35857-66-0 ]

* 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 [ 35857-66-0 ]

[ 35857-66-0 ] Synthesis Path-Downstream   1~59

  • 1
  • [ 35857-66-0 ]
  • [ 62847-55-6 ]
YieldReaction ConditionsOperation in experiment
With 3,5-dihydroxyphenol; sodium nitrite
  • 2
  • [ 95-50-1 ]
  • [ 625-36-5 ]
  • [ 35857-66-0 ]
YieldReaction ConditionsOperation in experiment
87.1% Stage #1: 2-chloropropionyl chloride With aluminum (III) chloride In chloroform at 20℃; for 1h; Stage #2: 1,2-dichloro-benzene In chloroform at 10 - 20℃; 4.1.1.1. 3-Chloro-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one (7a) General procedure: Aluminum chloride (8.4 g, 62.0 mmol) was added dropwise to a solution of 3-chloropropanoyl chloride (7.2 g, 57.0 mmol) in chloroform (70 mL) at room temperature. The reaction mixture was stirred at the same temperature for 1 h. After cooling to 10, a solution of 1-chloro-2-methoxynaphthalene (11.0 g, 57.0 mmol) in chloroform (25 mL) was added dropwise, and then the mixture was stirred at room temperature for 2.5 h. The reaction was complete as determined by thin layers chromatography (TLC) with EtOAc/hexane (1/15, v/v). The reaction mixture was poured slowly onto ice water, after stirred for 30 min, the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in reduced pressure. the crude product was purified by silica gel column chromatography with EtOAc/hexane (1/20, v/v) as mobile phase to give 7a (12.1 g, 75.0%) as a pale yellow solid.
86.9% With aluminum (III) chloride at 70℃; for 8h; 1 Method B General procedure: The aromatic compound (I) (0.2 mol) added with AlCl3 (0.24 mol) is heated to 70° C. and added dropwise the corresponding acyl chloride (VII) (0.2 mol) under stirring. After the addition, a reaction is maintained at 70° C. for 8 h. TLC with ethyl acetate: petroleum ether (1:15) indicates a completion of the reaction. The reaction mixture is cooled to room temperature and added with CH2Cl2 (100 mL) before it is poured into 50 mL ice water under stirring. The organic phase is separated and washed with saturated NaCl solution (50 mL×1). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated. A pure product of the halogenated aralkyl-ketone (II) is obtained with a yield of 80-90% by slurrying the concentrate in anhydrous ethanol (50 mL).
86.9% With aluminum (III) chloride at 70℃; for 8h; 1 Preparation of the halogenated aralkyl-ketone (II) General procedure: The aromatic compound (I) (0.2mol) added with AlCl3 (0.24mol) is heated to 70°C and added dropwise the corresponding acyl chloride (VII) (0.2mol) under stirring. After the addition, a reaction is maintaind at 70°C for 8h. TLC with ethyl acetate: petroleum ether (1:15) indicates a completion of the reaction. The reaction mixture is cooled to room temperature and added with CH2Cl2 (100mL) before it is poured into 50mL ice water under stirring. The organic phase is separated and washed with saturated NaCl solution (50mL 3 1). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated. A pure product of the halogenated aralkyl-ketone (II) is obtained with a yield of 80-90% by slurrying the concentrate in anhydrous ethanol (50mL).
80% With aluminum (III) chloride at 70℃; for 6h; 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) A mixture of 1,2-dichlorobenzene (50g, 340 mmol) and anhydrous AlCl3 (45.354 g, 340 mmol) was heated to 70 degree, following 3-chloropropanoyl chloride (47.506 g, 374 mmol) was added dropwise. The resulting mixture was stirred at 70 degree for 6 h. After cooling to room temperature, the mixture was diluted with DCM (300 mL). Then the mixture was poured slowly into ice-water (200 mL), stirred for 0.5h. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/hexane = 1/50, V/V) to give compound 2a as white solid (64.6 g, 80%).
With aluminium trichloride
Stage #1: 2-chloropropionyl chloride With aluminum (III) chloride In chloroform at 10 - 20℃; for 1h; Stage #2: 1,2-dichloro-benzene In chloroform at 20℃; for 2.5h; 4.1.4 General procedure for the synthesis of 1-aryl-3-chloropropan-1-ones (8) [15] General procedure: Aluminum chloride (8.4g, 62.0mmol) was added dropwise to a solution of 3-chloropropanoyl chloride (7.2g, 57.0mmol) in chloroform (70mL) at room temperature. The reaction mixture was stirred at the same temperature for 1h. After cooling to 10°C, a solution of aromatic ring (57.0mmol) in chloroform (25mL) was added dropwise, and then the mixture was stirred at room temperature for 2.5h. The reaction was complete as determined by thin layers chromatography (TLC) with EtOAc/hexane (1/15, v/v). The reaction mixture was poured slowly into ice water, after stirred for 30min, the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in reduced pressure. The crude product was purified by silica gel column chromatography with EtOAc/hexane (1/20, v/v) as mobile phase to give compound 8.

  • 3
  • [ 10467-10-4 ]
  • [ 35857-66-0 ]
  • [ 107049-58-1 ]
YieldReaction ConditionsOperation in experiment
98% In benzene for 1h;
  • 4
  • [ 917-64-6 ]
  • [ 35857-66-0 ]
  • [ 113696-78-9 ]
YieldReaction ConditionsOperation in experiment
93% In benzene for 1h;
  • 5
  • [ 35857-66-0 ]
  • [ 1889-20-9 ]
  • [ 113696-80-3 ]
YieldReaction ConditionsOperation in experiment
32% In benzene for 1h;
  • 6
  • [ 35857-66-0 ]
  • [ 37782-11-9 ]
  • [ 113696-83-6 ]
YieldReaction ConditionsOperation in experiment
93% In benzene for 1h;
  • 7
  • [ 35857-66-0 ]
  • [ 10557-57-0 ]
  • [ 113696-79-0 ]
YieldReaction ConditionsOperation in experiment
32% In benzene for 1h;
  • 8
  • [ 35857-66-0 ]
  • [ 3814-99-1 ]
  • [ 113696-81-4 ]
YieldReaction ConditionsOperation in experiment
48% In benzene for 1h;
  • 9
  • [ 35857-66-0 ]
  • [ 89583-95-9 ]
  • [ 113696-82-5 ]
YieldReaction ConditionsOperation in experiment
47% In benzene for 1h;
  • 10
  • [ 35857-66-0 ]
  • [ 107049-57-0 ]
  • [ 113720-98-2 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine In xylene for 9h; Heating;
  • 11
  • [ 35857-66-0 ]
  • [ 113696-63-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / benzene / 1 h 2: 57 percent / triethylamine (Et3N) / xylene / Heating
  • 12
  • [ 35857-66-0 ]
  • [ 113696-66-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / benzene / 1 h 2: 44 percent / triethylamine (Et3N) / xylene / Heating
  • 13
  • [ 35857-66-0 ]
  • 2C26H36Cl2N2O4*4ClH*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / benzene / 1 h 2: 49 percent / triethylamine (Et3N) / xylene / Heating
  • 14
  • [ 35857-66-0 ]
  • C27H38Cl2N2O4*2ClH*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 32 percent / benzene / 1 h 2: 40 percent / triethylamine (Et3N) / xylene / Heating
  • 15
  • [ 35857-66-0 ]
  • 2C28H40Cl2N2O4*4ClH*3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 48 percent / benzene / 1 h 2: 11 percent / triethylamine (Et3N) / xylene / Heating
  • 16
  • [ 35857-66-0 ]
  • 2C29H42Cl2N2O4*4ClH*3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 47 percent / benzene / 1 h 2: 16 percent / triethylamine (Et3N) / xylene / Heating
  • 17
  • [ 35857-66-0 ]
  • [ 113721-01-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / triethylamine (Et3N) / xylene / 9 h / Heating 2: 17 percent / benzene / 2 h
  • 18
  • [ 35857-66-0 ]
  • 2C30H36Cl2N2O4*4ClH*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 93 percent / benzene / 1 h 2: 29 percent / triethylamine (Et3N) / xylene / Heating
  • 19
  • [ 35857-66-0 ]
  • [ 113721-03-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / triethylamine (Et3N) / xylene / 9 h / Heating 2: 24 percent / benzene / 2 h
  • 20
  • [ 35857-66-0 ]
  • [ 113721-06-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / triethylamine (Et3N) / xylene / 9 h / Heating 2: 30 percent / benzene / 2 h
  • 21
  • [ 35857-66-0 ]
  • [ 113721-09-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / triethylamine (Et3N) / xylene / 9 h / Heating 2: 24 percent / benzene / 2 h
  • 22
  • [ 35857-66-0 ]
  • [ 56045-67-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaNO2, benzene-1,3,5-triol 2: aq. HCl
  • 23
  • [ 37581-40-1 ]
  • [ 35857-66-0 ]
  • [ 1394204-81-9 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; 4.1.4.1. 3-(4-Benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(5-chloro-6-methoxynaphthalen -2-yl)propan-1-one hydrochloride (5k) General procedure: To a stirred mixture of compounds 3-chloro-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one (2.0 g, 7.1 mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1 g, 6.4 mmol) in CH3CN (20 mL) was added N,N-Diisopropylethylamine (1.7 g, 12.9 mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with CH2Cl2 (30 mL) and water (130 mL). The organic layer was washed with brine (20 mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10 mL) was added hydrogen chloride ethanol solution (1.25 M, 8 mL) dropwise, and the resulting mixture was stirred for 1 h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 5k (2.4 g, 81.9%) as a white solid.
  • 24
  • 4-benzylpiperidin-4-ol hydrochloride [ No CAS ]
  • [ 35857-66-0 ]
  • [ 1394204-80-8 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; 4.1.4.1. 3-(4-Benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(5-chloro-6-methoxynaphthalen -2-yl)propan-1-one hydrochloride (5k) General procedure: To a stirred mixture of compounds 3-chloro-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one (2.0 g, 7.1 mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1 g, 6.4 mmol) in CH3CN (20 mL) was added N,N-Diisopropylethylamine (1.7 g, 12.9 mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with CH2Cl2 (30 mL) and water (130 mL). The organic layer was washed with brine (20 mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10 mL) was added hydrogen chloride ethanol solution (1.25 M, 8 mL) dropwise, and the resulting mixture was stirred for 1 h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 5k (2.4 g, 81.9%) as a white solid.
  • 25
  • [ 35857-66-0 ]
  • [ 1394204-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C 3: sodium tetrahydroborate / methanol / 2 h / 20 °C
  • 26
  • [ 35857-66-0 ]
  • [ 1394204-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C 3: sodium tetrahydroborate / methanol / 2 h / 20 °C
  • 27
  • [ 35857-66-0 ]
  • [ 1394148-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C
  • 28
  • [ 35857-66-0 ]
  • [ 1394148-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C
  • 29
  • [ 35857-66-0 ]
  • [ 1394147-55-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C 3: sodium tetrahydroborate / methanol / 2 h / 20 °C 4: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C
  • 30
  • [ 35857-66-0 ]
  • [ 1394147-57-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C 3: sodium tetrahydroborate / methanol / 2 h / 20 °C 4: hydrogenchloride / ethanol; ethyl acetate / 1 h / 20 °C
  • 31
  • [ 35857-66-0 ]
  • [ 1346461-00-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 3 h / 20 °C
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 1.2: 1 h / 20 °C 2.1: sodium tetrahydroborate / methanol / 2 h / 20 °C 2.2: 1 h / 20 °C
  • 32
  • [ 35857-66-0 ]
  • [ 1346460-37-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / ethanol / 12 h / 20 °C 2.1: sodium tetrahydroborate / methanol / 3 h / 20 °C 3.1: triethylamine; toluene-4-sulfonic acid / acetonitrile / 12 h / 20 °C 3.2: 8 h / 20 °C
  • 33
  • [ 35857-66-0 ]
  • [ 660-68-4 ]
  • 1-(3,4-Dichloro-phenyl)-3-diethylamino-propan-1-one; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.9% Stage #1: 3-chloro-1-(3,4-dichlorophenyl)propan-1-one; diethyl amine hydrochloride With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 12h; Stage #2: With hydrogenchloride In ethyl acetate 1 Method B General procedure: A reaction mixture of the halogenated aralkyl-ketone (II) (0.1 mol) and the hydrochloride of the amine (VIII) (0.1 mol) as a starting material dissolved in acetonitrile (100 mL) is added with diisopropylethylamine (0.2 mol) and reacted at room temperature for 12 h. TLC (dichloromethane: methanol=20:1) indicates a complete consumption of the starting material (II). The solvent is concentrated down till dry. To the residue, dichloromethane (100 mL) and saturated NaCl solution (40 mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt % dilute HCl solution (30 mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30 mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 60-85% based on the intermediate (II).
  • 34
  • [ 35857-66-0 ]
  • [ 124-40-3 ]
  • [ 75144-12-6 ]
YieldReaction ConditionsOperation in experiment
81.9% General procedure: A reaction mixture of the halogenated aralkyl-ketone (II) (0.1 mol) and the amine (VIII) (0.5 mol) as a starting material dissolved in anhydrous ethanol (100 mL) is reacted under reflux for 3 h. TLC (dichloromethane: methanol=20:1) indicates a complete consumption of the starting material (II). The solvent is concentrated down till dry. To the residue, dichloromethane (100 mL) and saturated NaCl solution (40 mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt % dilute HCl solution (30 mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30 mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 70-95% based on the intermediate (II).
  • 35
  • [ 35857-66-0 ]
  • [ 13426-94-3 ]
  • [ 1346596-04-0 ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 5 Preparation of aralkyl-ketone amine, the intermediate (III) General procedure: A reaction mixture of the halogenated aralkyl-ketone (II) (0.1mol) and the hydrochloride of the amine (VIII) (0.1mol) as a starting material dissolved in acetonitrile (100mL) is added with diisopropylethylamine (0.2mol) and reacted at room temperature for 12h. TLC (dichloromethane: methanol = 20: 1) indicates a complete consumption of the starting material (II). The solvent is concentrated down till dry. To the residue, dichloromethane (100mL) and saturated NaCl solution (40mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt% dilute HCl solution (30mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 60-85% based on the intermediate (II).
Stage #1: 3-chloro-1-(3,4-dichlorophenyl)propan-1-one; N-methylbenzylamine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 36
  • [ 35857-66-0 ]
  • [ 1226129-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate; methanol / 3 h / 20 °C
  • 37
  • [ 35857-66-0 ]
  • C20H25Cl2NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate; methanol / 3 h / 20 °C 3: triethylamine / acetonitrile / 12 h / 20 °C
  • 38
  • [ 35857-66-0 ]
  • [ 109-89-7 ]
  • C13H17Cl2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.7% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1 Preparation of aralkyl-ketone amine, the intermediate (III) General procedure: A reaction mixture of the halogenated aralkyl-ketone (II) (0.1mol) and the hydrochloride of the amine (VIII) (0.1mol) as a starting material dissolved in acetonitrile (100mL) is added with diisopropylethylamine (0.2mol) and reacted at room temperature for 12h. TLC (dichloromethane: methanol = 20: 1) indicates a complete consumption of the starting material (II). The solvent is concentrated down till dry. To the residue, dichloromethane (100mL) and saturated NaCl solution (40mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt% dilute HCl solution (30mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 60-85% based on the intermediate (II).
  • 39
  • [ 35857-66-0 ]
  • [ 124-40-3 ]
  • [ 50516-63-7 ]
YieldReaction ConditionsOperation in experiment
81.9% In ethanol for 3h; Reflux; 2 Preparation of aralkyl-ketone amine, the intermediate (III) General procedure: A reaction mixture of the halogenated aralkyl-ketone (II) (0.1mol) and the amine (VIII) (0.5mol) as a starting material dissolved in anhydrous ethanol (100mL) is reacted under reflux for 3h. TLC (dichloromethane: methanol = 20:1) indicates a complete consumption of the starting material (II). The solvent is concentrated down till dry. To the residue, dichloromethane (100mL) and saturated NaCl solution (40mL) are added, followed by a 20-min stirring. The organic phase is separated and washed with 5 wt% dilute HCl solution (30mL). After dried over anhydrous MgSO4, the organic phase is filtered and then concentrated to give the crude product which is then dissolved in ethyl acetate (30mL) and formed a hydrochloride by adding hydrochloric acid alcohol to the mixture. The intermediate (III) is thus obtained with a yield of 70-95% based on the intermediate (II).
  • 40
  • [ 35857-66-0 ]
  • N,N-diethyl-3-(3,4-dichlorophenyl)-3-(pyrrolidin-1-yl)propylamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate; methanol / 3 h / 20 °C 3: triethylamine / acetonitrile / 12 h / 20 °C 4: potassium carbonate / acetonitrile / 8 h / 20 °C
  • 41
  • [ 35857-66-0 ]
  • [ 1346461-03-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 1.2: 1 h / 20 °C 2.1: sodium tetrahydroborate / methanol / 2 h / 20 °C 2.2: 1 h / 20 °C
  • 42
  • [ 35857-66-0 ]
  • [ 1346461-01-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 1.2: 1 h / 20 °C 2.1: sodium tetrahydroborate / methanol / 2 h / 20 °C 2.2: 1 h / 20 °C
  • 43
  • [ 35857-66-0 ]
  • [ 660-68-4 ]
  • C13H17Cl2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-chloro-1-(3,4-dichlorophenyl)propan-1-one; diethyl amine hydrochloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 44
  • [ 110-89-4 ]
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(piperidin-1-yl)propan-1-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.7% Stage #1: piperidine; 3-chloro-1-(3,4-dichlorophenyl)propan-1-one With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 45
  • [ 110-91-8 ]
  • [ 35857-66-0 ]
  • [ 27922-20-9 ]
YieldReaction ConditionsOperation in experiment
81.7% Stage #1: morpholine; 3-chloro-1-(3,4-dichlorophenyl)propan-1-one With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 46
  • [ 35857-66-0 ]
  • [ 506-59-2 ]
  • [ 50516-63-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-chloro-1-(3,4-dichlorophenyl)propan-1-one; N,N-dimethylammonium chloride With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 47
  • [ 37581-40-1 ]
  • [ 35857-66-0 ]
  • [ 1394148-14-1 ]
YieldReaction ConditionsOperation in experiment
76.9% Stage #1: 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride; 3-chloro-1-(3,4-dichlorophenyl)propan-1-one With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Stage #2: With hydrogenchloride In ethanol; ethyl acetate at 20℃; for 1h; 4.1.5 Procedure D. General procedure for the synthesis of aryl ketone 9[15] General procedure: To a stirred mixture of ketone 8 (7.1mmol) and 4-benzyl-1,2,3,6-tetrahydropyridine hydrochloride (1.1g, 6.4mmol) in acetonitrile (20mL) was added diisopropylethylamine (1.7g, 12.9mmol). After being stirred overnight at room temperature, the solvent was removed under reduced pressure. The crude residue was extracted with dichloromethane (30mL) and water (30mL). The organic layer was washed with brine (20mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (10mL) and hydrogen chloride ethanol solution (1.25M, 8mL) was added dropwise, the resulting mixture was stirred for 1h at room temperature to give a hydrochloride product. The white solid was filtered, washed thoroughly with ethyl acetate and ethanol, separately, and to give compound 9.
  • 48
  • [ 35857-66-0 ]
  • (R)-3-chloro-1-(3,4-dichlorophenyl)propan-1-ol [ No CAS ]
  • (S)-3-chloro-1-(3,4-dichlorophenyl)propan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
60 % ee With diborane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; 2-methyltetrahydrofuran at 0℃; Flow reactor; Green chemistry; Overall yield = 66 %; Overall yield = 94 mg; enantioselective reaction;
  • 49
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)-1-piperazinyl)propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C
  • 50
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(4-(2-methylthiophenyl)-1-piperazinyl)propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C
  • 51
  • [ 35857-66-0 ]
  • 2-(4-(3-(3,4-dichlorophenyl)-3-hydroxypropyl)-1-piperazinyl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C
  • 52
  • [ 35857-66-0 ]
  • 3-(4-([1,1'-biphenyl]-2-yl)-1-piperazinyl)-1-(3,4-dichlorophenyl)propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C
  • 53
  • [ 35857-66-0 ]
  • 3-(4-([1,1'-biphenyl]-3-yl)-1-piperazinyl)-1-(3,4-dichlorophenyl)propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 12 h / 20 °C 2: sodium tetrahydroborate / methanol / 5 h / 0 - 20 °C
  • 54
  • [ 35386-24-4 ]
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one (3a) A mixture of 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) (250 mg, 1.05mmol ), 1-(2-methoxyphenyl)piperazine (223 mg, 1.16 mmol) and DIPEA (272 mg, 2.1 mmol ) in CH3CN (20 mL) was stirred R.T. for 12 h. The solvent was removed under reduced pressure, then DCM (30 mL) was added. The mixture was washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/MeOH = 50/1, V/V) to give compound 3a as pale-yellow slid (344 mg, 83%).
  • 55
  • [ 1013-24-7 ]
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(4-(2-(methylthio)phenyl)piperazin-1-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one (3a) General procedure: A mixture of 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) (250 mg, 1.05mmol ), 1-(2-methoxyphenyl)piperazine (223 mg, 1.16 mmol) and DIPEA (272 mg, 2.1 mmol ) in CH3CN (20 mL) was stirred R.T. for 12 h. The solvent was removed under reduced pressure, then DCM (30 mL) was added. The mixture was washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/MeOH = 50/1, V/V) to give compound 3a as pale-yellow slid (344 mg, 83%).
  • 56
  • [ 1011-17-2 ]
  • [ 35857-66-0 ]
  • 1-(3,4-dichlorophenyl)-3-(4-(2-hydroxyphenyl)piperazin-1-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one (3a) General procedure: A mixture of 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) (250 mg, 1.05mmol ), 1-(2-methoxyphenyl)piperazine (223 mg, 1.16 mmol) and DIPEA (272 mg, 2.1 mmol ) in CH3CN (20 mL) was stirred R.T. for 12 h. The solvent was removed under reduced pressure, then DCM (30 mL) was added. The mixture was washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/MeOH = 50/1, V/V) to give compound 3a as pale-yellow slid (344 mg, 83%).
  • 57
  • [ 35857-66-0 ]
  • [ 180698-18-4 ]
  • 3-(4-([1,1'-biphenyl]-2-yl)piperazin-1-yl)-1-(3,4-dichlorophenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one (3a) General procedure: A mixture of 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) (250 mg, 1.05mmol ), 1-(2-methoxyphenyl)piperazine (223 mg, 1.16 mmol) and DIPEA (272 mg, 2.1 mmol ) in CH3CN (20 mL) was stirred R.T. for 12 h. The solvent was removed under reduced pressure, then DCM (30 mL) was added. The mixture was washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/MeOH = 50/1, V/V) to give compound 3a as pale-yellow slid (344 mg, 83%).
  • 58
  • [ 115761-61-0 ]
  • [ 35857-66-0 ]
  • 3-(4-([1,1'-biphenyl]-3-yl)piperazin-1-yl)-1-(3,4-dichlorophenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; 1-(3,4-dichlorophenyl)-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-1-one (3a) General procedure: A mixture of 3-chloro-1-(3,4-dichlorophenyl)propan-1-one (2a) (250 mg, 1.05mmol ), 1-(2-methoxyphenyl)piperazine (223 mg, 1.16 mmol) and DIPEA (272 mg, 2.1 mmol ) in CH3CN (20 mL) was stirred R.T. for 12 h. The solvent was removed under reduced pressure, then DCM (30 mL) was added. The mixture was washed with water and brine, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/MeOH = 50/1, V/V) to give compound 3a as pale-yellow slid (344 mg, 83%).
  • 59
  • [ 35857-66-0 ]
  • [ 87691-88-1 ]
  • C20H19Cl2N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 12h; General procedure: The arylhaloketone (I) (0.1 mol) and the hydrochloride salt of piperazine (pyridinium) compound (II) (0.1 mol) were dissolved in acetonitrile (100 mL) and diisopropylethylamine (0.2 mol) was added.After 12 h at room temperature, TLC (methylene chloride:methanol=20:1) showed that the reaction of starting material (I) was complete.The solvent was concentrated to dryness, and dichloromethane (100 mL) and saturated brine (40 mL) were added and the mixture was stirred for 20 min.The organic layer was dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography (eluent:Dichloromethane/methanol = 30:1) gave intermediate (III) in a yield of 60-85% (based on arylhaloketone I).
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