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[ CAS No. 781-35-1 ] {[proInfo.proName]}

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Chemical Structure| 781-35-1
Chemical Structure| 781-35-1
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Product Details of [ 781-35-1 ]

CAS No. :781-35-1 MDL No. :MFCD00008759
Formula : C15H14O Boiling Point : -
Linear Structure Formula :- InChI Key :DBNWBEGCONIRGQ-UHFFFAOYSA-N
M.W : 210.27 Pubchem ID :69907
Synonyms :

Safety of [ 781-35-1 ]

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 [ 781-35-1 ]

* 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 [ 781-35-1 ]

[ 781-35-1 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 50-00-0 ]
  • [ 781-35-1 ]
  • [ 6091-44-7 ]
  • [ 103281-49-8 ]
  • 2
  • [ 781-35-1 ]
  • [ 131-11-3 ]
  • [ 82-66-6 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate
  • 3
  • [ 781-35-1 ]
  • [ 33609-25-5 ]
YieldReaction ConditionsOperation in experiment
With bromine; acetic acid
With bromine In acetic acid; toluene 21 3-Diphenylmethyl-2,3,6,7-tetrahydro-5H-thiazolo[3,2]-a]pyrimidin-3-ol hydrobromide EXAMPLE 21 3-Diphenylmethyl-2,3,6,7-tetrahydro-5H-thiazolo[3,2]-a]pyrimidin-3-ol hydrobromide A solution of 2.1 g. of 1,1-diphenyl-2-propanone in 25 ml. of acetic acid is heated to 60°-70° C. and 0.5 ml. of bromine in 4 ml. of acetic acid is added dropwise. The reaction mixture is held at 60°-70° C. for one hour and then poured into ice. Toluene is added. The toluene layer is separated, washed with water, dried over magnesium sulfate and concentrated, giving 1-bromo-3,3-diphenyl-2-propanone.
With bromine In acetic acid; toluene 22 3-Diphenylmethyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrobromide EXAMPLE 22 3-Diphenylmethyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrobromide A solution of 4.20 g. of 1,1-diphenyl-2-propanone in 25 ml. of acetic acid is heated at 60°-70° C. and 1.0 ml. of bromine in 8 ml. of acetic acid is added dropwise. The reaction mixture is held at 60°-70° C. for one hour and then poured into ice. Toluene is added. The toluene layer is separated, washed with water, dried over magnesium sulfate and concentrated to obtain 1-bromo-3,3-diphenyl-2-propanone.
With bromine In acetic acid; toluene 84 3-Diphenylmethyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrobromide EXAMPLE 84 3-Diphenylmethyl-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrobromide A solution of 4.20 g. (0.02 mol) of 1,1-diphenyl-2-propanone in 25 ml. of acetic acid is heated at 60°--70° C. and 1.0 ml. (0.02 mol) of bromine in 8 ml. of acetic acid is added dropwise. The reaction mixture is held at 60°-70° C. for one hour and then poured into ice. Toluene is added. The toluene layer is separated, washed with water, dried over magnesium sulfate and concentrated to obtain 1-bromo-3,3-diphenyl-2-propanone.
With bromine In acetic acid 1 3-Bromo-1,1-diphenyl-2-propanone EXAMPLE 1 3-Bromo-1,1-diphenyl-2-propanone The subject compound is prepared essentially by the procedure of C. L. Stevens and C. T. Lenh, J. Org. Chem. 19, 538 (1954). To a stirred solution of 42.0 g. of 1,1-diphenyl-2-propanone in 150 ml. of glacial acetic acid at 60°-70° C., is added dropwise, over 45 minutes, a solution of 32.0 of bromine in 25 ml. of glacial acetic acid. The mixture is then stirred for one hour at 60°-70° C. The mixture is poured into 500 ml. of ice, allowed to stand in a refrigerator overnight, and the solid is collected by filtration, washed with water and ice-cold isopropanol, and recrystallized from isopropanol, giving 29.0 of the desired product as light pink crystals, m.p. 62°-64° C.
52 g With bromine; acetic acid at 60℃; for 1.5h; Inert atmosphere; 3 10167] To a solution ofA-i (50 g, 237 mmol) mAcOH (250 mE) at 60° C. under N2 was added 13r2 (38.0 g, 237 mmol) dropwise. After addition (30 mm), the mixture was stirred at the same temperature for 1 h. The solution was then cooled to RT and then poured into ice-water (250 mE). The reaction was quenched with saturated aq. Na2503. The mixture was extracted with DCM (3x250 mE). The combined organic layers were washed with aq. NaHCO3 and brine, and dried over Na2504. The mixture was filtered and concentrated. To the residue was added with PE (200 mE). The mixture was violently stirred for 20 mins and then filtered. The filtrate cake was washed with PE and dried in vacuum to provide crude A-2 as a white solid (52 g), which was used directly in the next step without further purification.

  • 7
  • [ 781-35-1 ]
  • [ 1530-03-6 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; hydrazine hydrate; diethylene glycol at 210℃;
  • 8
  • [ 781-35-1 ]
  • 1,1-diphenyl-2-propanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; methanol Flow reactor;
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether
With hydrogen In diethylene glycol dimethyl ether; water at 30℃; for 5h;
With sodium tetrahydroborate In ethanol Inert atmosphere;
With C38H38IrN4S2(1+)*F6P(1-); ammonium formate; 3-methyl-5-p-methoxyphenyl-1-hydropyrazole In tetrahydrofuran; water at 40℃;
Multi-step reaction with 2 steps 1: iron(III)-acetylacetonate; sodium triethylborohydride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox 2: sodium hydroxide; dihydrogen peroxide / 1 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox

  • 10
  • [ 781-35-1 ]
  • [ 118573-92-5 ]
YieldReaction ConditionsOperation in experiment
90% With ammonia; hydrogen In tetrahydrofuran at 120℃; for 20h;
(i) NH2OH, (ii) H2, Raney-Ni, aq. NaOH, EtOH; Multistep reaction;
(i) HCONH2, (heating), (ii) aq. HCl; Multistep reaction;
With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; for 40h;

  • 11
  • [ 781-35-1 ]
  • [ 57272-43-2 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate; oxygen In N,N-dimethyl-formamide
  • 12
  • [ 69034-90-8 ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In methanol Ambient temperature;
  • 13
  • [ 5815-08-7 ]
  • [ 781-35-1 ]
  • [ 143547-74-4 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate 1.) 110 deg C, 30 min, 2.) 120 deg C, 30 min; Yield given. Multistep reaction;
  • 14
  • [ 781-35-1 ]
  • [ 28178-42-9 ]
  • N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-γ-phenyl-benzenebutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide 1.) ether, -78 deg C, 20 min, 2.) ether, from -78 deg C to RT, 16 h; Multistep reaction;
With lithium diisopropyl amide 2 Preparation of N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-γ-phenyl-benzenebutanamide EXAMPLE 2 Preparation of N-[2,6-bis(1-methylethyl)phenyl]-β-oxo-γ-phenyl-benzenebutanamide The title compound, mp 153°-155° C., was prepared from 1,1-diphenylacetone (5.0 g, 0.023 mol), 2,6-diisopropylphenyl isocyanate (4.6 g, 0.023 mol) and lithium diisopropylamide (0.023 mol) using the procedure described in Example 1. Analysis for C28 H31 NO2: Calcd: C, 81.31; H, 7.55; N, 3.38; Found: C, 80.75; H, 7.84; N, 3.01.
  • 15
  • [ 781-35-1 ]
  • [ 135664-25-4 ]
YieldReaction ConditionsOperation in experiment
87% With sodium dodecyl-sulfate; Selectfluor In water at 80℃; Micellar solution; regioselective reaction;
81% With N-fluorobis<(trifluoromethyl)sulfonyl>imide In chloroform at 22℃; for 6h;
  • 16
  • [ 6337-69-5 ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
81% With dinitrogen tetraoxide In acetonitrile at -40℃; for 0.166667h;
81% With dinitrogen tetraoxide In acetonitrile at -40℃; for 0.166667h;
  • 17
  • [ 15795-69-4 ]
  • [ 781-35-1 ]
  • [ 6337-69-5 ]
YieldReaction ConditionsOperation in experiment
1: 27% 2: 56% With titanium(III) chloride In tetrahydrofuran; water at 0℃; for 20h; pH 6.5;
1: 27% 2: 56% With titanium(III) chloride; ammonium acetate In tetrahydrofuran; water at 0℃; for 20h;
  • 18
  • [ 15795-69-4 ]
  • [ 781-35-1 ]
  • [ 105381-45-1 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 84% With titanium(III) chloride In tetrahydrofuran; water at 35℃; for 24h; pH 6.5;
1: 14% 2: 84% With titanium(III) chloride; ammonium acetate In tetrahydrofuran; water at 35℃; for 24h;
  • 19
  • [ 74050-54-7 ]
  • [ 781-35-1 ]
  • [ 2042-85-5 ]
YieldReaction ConditionsOperation in experiment
1: 72% 2: 24% With diethylaluminum benzenethiolate In hexane at 25℃; for 0.2h; Title compound not separated from byproducts;
  • 20
  • [ 781-35-1 ]
  • [ 459-57-4 ]
  • 4-(4-Fluorophenyl)-1,1-diphenyl-3-buten-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With sodium ethanolate; acetic acid In ethanol 60.A A. A. 4-(4-Fluorophenyl)-1,1-diphenyl-3-buten-2-one A mixture of 4-fluorobenzaldehyde (3.54 gm, 28.5 mmol) and 1,1-diphenylacetone (5.000 gm, 23.8 mmol) in absolute EtOH (50 ml) was treated with a solution of EtONa in EtOH (21% solution, 900 μl, 2.4 mmol). After stirring at room temperature for 22 hours, the mixture was concentrated to 35 ml and the solution was treated with HOAc (200 mg). The solution was cooled to 0° C. and the precipitate that had formed was collected by filtration and washed with cold EtOH. The title compound was obtained as a pale yellow solid (5.787 gm, 77%). m.p. 122°-124° C. TLC: Rf 0.32 (20% EtOAc in hexane)
With sodium ethanolate In ethanol for 15h; Ambient temperature;
  • 21
  • [ 24834-34-2 ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
100% With Dowex 50W ion-exchange resin In dichloromethane Heating;
  • 22
  • [ 113388-56-0 ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride In tetrahydrofuran; water for 48h; Ambient temperature;
  • 23
  • [ 781-35-1 ]
  • [ 1068-57-1 ]
  • [ 141981-35-3 ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid In ethanol for 24h; Heating;
  • 25
  • [ 781-35-1 ]
  • [ 140-88-5 ]
  • [ 13128-74-0 ]
YieldReaction ConditionsOperation in experiment
98% With potassium <i>tert</i>-butylate In various solvent(s) at 20℃;
92% With potassium <i>tert</i>-butylate In diethyl ether for 18h; Ambient temperature;
44% With potassium <i>tert</i>-butylate In diethyl ether at 20℃; for 9h; Inert atmosphere;
Stage #1: 1,1-diphenylacetone With potassium <i>tert</i>-butylate In diethyl ether for 0.166667h; Stage #2: ethyl acrylate In diethyl ether at 20℃; Intermediate 12-4,4-Diphenyl-cyclohexane-1,3-dione To a stirring suspension of 2.8 g (0.025 mole) of potassium t-butoxide in 50 ml ethyl ether was added 0.53 g (0.025 mole) of 1,1 diphenylacetone in 25 ml ethyl ether. The reaction was stirred for ten minutes; the white slurry became a clear yellow solution. 2.7 ml (0.025 mole) of ethyl acrylate in 50 ml ethyl ether was added. A white precipitate formed immediately. The reaction was stirred overnight at room temperature. The white precipitate was collected on a filter and washed with ethyl ether. The crude product was dissolved in water, acidified with dilute HCl and extracted (three times) into chloroform. The combined chloroform extracts were dried over sodium sulfate, filtered and stripped to a solid (4.1 g). MS: (-) ES (M-H)- 263, Elemental Anal. Calcd. for C18H16O2+0.5 mole H2O: C, 79.10%; H, 6.27%; N, 0.00%, Found: C, 79.09%; H, 5.90%; N, 0.02%, 1H-NMR (DMSO-d6) δ 11.13 (b, 1H); 7.27 (m, 6H); 7.10 (m, 4H); 5.38 (s,1H); 2.64 (m, 2H); (s, 2H).

  • 26
  • 1,2-diphenyl-1-phenylthio-2-propanol [ No CAS ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
69% With tetraethylammonium chloride In methanol; dichloromethane electrolysis;
  • 27
  • [ 17789-14-9 ]
  • [ 781-35-1 ]
  • 3-(3-[1,3]Dioxolan-2-yl-phenyl)-1,1-diphenyl-propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tol-BINAP; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In tetrahydrofuran at 70℃;
  • 28
  • [ 781-35-1 ]
  • [ 5892-99-9 ]
  • N,N-Diethyl-4-(2-oxo-3,3-diphenyl-propyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tol-BINAP; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In tetrahydrofuran at 70℃;
  • 29
  • [ 781-35-1 ]
  • [ 117-34-0 ]
YieldReaction ConditionsOperation in experiment
95% With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 2h;
  • 30
  • [ 37595-74-7 ]
  • [ 781-35-1 ]
  • [ 29571-19-5 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 1,1-diphenylacetone With sodium hydride In tetrahydrofuran at 0℃; for 2h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 0 - 20℃;
With sodium hydride 1.) DMF, mineral oil, 2 h, 2.) DMF, mineral oil, overnight; Yield given. Multistep reaction;
  • 31
  • [ 50-00-0 ]
  • [ 781-35-1 ]
  • [ 6091-44-7 ]
  • [ 5446-73-1 ]
YieldReaction ConditionsOperation in experiment
With lead acetate at 280℃;
  • 33
  • [ 75-77-4 ]
  • [ 781-35-1 ]
  • [ 51425-63-9 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 48h; Further stages.;
  • 34
  • [ 13154-24-0 ]
  • [ 781-35-1 ]
  • triisopropyl-(1-methyl-2,2-diphenyl-vinyloxy)-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran at 20℃; for 48h; Further stages.;
  • 35
  • [ 781-35-1 ]
  • [ 18162-48-6 ]
  • [ 169696-27-9 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 48h; Further stages.;
  • 36
  • [ 623-26-7 ]
  • [ 75-77-4 ]
  • [ 781-35-1 ]
  • (Z,Z)-α,α'-bis[3,3-diphenyl-2-(trimethylsilyloxy)-2-propenylidene]-N,N'-bis(trimethylsilyl)-1,4-benzenedimethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: terephthalonitrile With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;
  • 37
  • [ 100-70-9 ]
  • [ 75-77-4 ]
  • [ 781-35-1 ]
  • (Z,Z)-[3,3-diphenyl-2-(trimethylsilyloxy)-2-propenylidene]-N-(trimethylsilyl)-[(2-pyridine)methanamine] [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-Cyanopyridine With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;
  • 38
  • [ 75-77-4 ]
  • [ 781-35-1 ]
  • [ 100-47-0 ]
  • (Z,Z)-[3,3-diphenyl-2-(trimethylsilyloxy)-2-propenylidene]-N-(trimethylsilyl)benzenemethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 1,1-diphenylacetone With potassium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: benzonitrile With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; Stage #3: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;
  • 39
  • 3-methyl-2,2-diphenyl-1-(toluene-4-sulfonyl)-aziridine [ No CAS ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
65% With boron trifluoride diethyl etherate In chloroform at -40 - 20℃; for 168h;
  • 40
  • [ 781-35-1 ]
  • [ 536-74-3 ]
  • [ 40650-77-9 ]
YieldReaction ConditionsOperation in experiment
10% With gallium(III) trichloride In dichloromethane for 54h; Heating;
  • 41
  • 1,1-diphenyl-2-propanol [ No CAS ]
  • [ 781-35-1 ]
  • (S)-(-)-1,1-diphenylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 38% 2: 57% With 3 A molecular sieve; oxygen; (-)-sparteine In <i>tert</i>-butyl alcohol at 65℃; for 24h;
  • 42
  • 1,1-diphenyl-2-propanol [ No CAS ]
  • [ 781-35-1 ]
  • (S)-(-)-1,1-diphenylpropan-2-ol [ No CAS ]
  • (R)-(+)-1,1-diphenylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3 A molecular sieve; oxygen; sodium carbonate In <i>tert</i>-butyl alcohol at 65℃; for 24h; Title compound not separated from byproducts;
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; bis(triphenylphosphine)iminium chloride; acetone; potassium hydroxide; N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane In dichloromethane; water; isopropyl alcohol at 45℃; for 32h; Resolution of racemate; Inert atmosphere; enantioselective reaction;
  • 43
  • [ 781-35-1 ]
  • [ 95-92-1 ]
  • 2,4-dioxo-5,5-diphenyl-pentanoic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate In tetrahydrofuran at 20℃;
  • 44
  • [ 781-35-1 ]
  • [ 109-94-4 ]
  • [ 143547-74-4 ]
YieldReaction ConditionsOperation in experiment
40% With sodium methylate; hydrazine In isopropyl alcohol; toluene
  • 45
  • [ 4741-91-7 ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
99% With rhenium(I) pentacarbonyl bromide In monoethylene glycol diethyl ether at 80℃; for 1h; Inert atmosphere; chemoselective reaction; 2. General Procedure General procedure: A 1,2-dichloroethane (2 mL) solution of oxirane (0.3 mmol) and ReBr(CO)5 (5 mol %) was stirred under an atmosphere of nitrogen at 80 °C for 1-5 h. After the reaction was complete, H2O was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with MgSO4. The resulting mixture was filtered, and the filtrate was concentrated. Purification of the residue by silica gel column chromatography afforded carbonyl compounds. Further purification was carried out by recyclable preparative HPLC, if necessary. The structures of the products were assigned by their 1H and 13C-NMR, and mass spectra. The products were characterized by comparing their 1H and 13C-NMR spectra data with those of authentic sample or previous reports. Yields were determined by 1H-NMR using internal standard.
With zeolite at 20℃; for 24h;
  • 46
  • [ 5162-44-7 ]
  • [ 781-35-1 ]
  • [ 752207-03-7 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: 1-bromo-4-butene In tetrahydrofuran at 20℃;
  • 47
  • [ 4894-61-5 ]
  • [ 781-35-1 ]
  • [ 119296-87-6 ]
  • [ 107556-98-9 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: trans-but-2-enyl chloride In tetrahydrofuran at 20℃; Title compound not separated from byproducts;
  • 48
  • [ 111-26-2 ]
  • [ 781-35-1 ]
  • [ 7501-79-3 ]
  • [ 101-81-5 ]
YieldReaction ConditionsOperation in experiment
1: 74% 2: 65% With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0 - 20℃; for 5.5h;
  • 49
  • [ 7348-78-9 ]
  • [ 781-35-1 ]
  • [ 752207-00-4 ]
YieldReaction ConditionsOperation in experiment
23% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: (Z)-1-bromo-2-pentene In tetrahydrofuran
  • 50
  • [ 2441-97-6 ]
  • [ 781-35-1 ]
  • [ 752207-01-5 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: 3-chloro-cyclohexene In tetrahydrofuran at 20℃;
  • 51
  • [ 781-35-1 ]
  • [ 37677-17-1 ]
  • [ 752207-02-6 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: 1-bromomethylcyclohexene In tetrahydrofuran at 20℃;
  • 52
  • [ 781-35-1 ]
  • [ 781-03-3 ]
  • [ 752207-04-8 ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: isopentenyl tosylate In tetrahydrofuran at 20℃;
  • 53
  • [ 781-35-1 ]
  • [ 106-95-6 ]
  • [ 107556-96-7 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: allyl bromide In tetrahydrofuran at 20℃;
  • 54
  • [ 781-35-1 ]
  • [ 870-63-3 ]
  • [ 107557-03-9 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 1,1-diphenylacetone With lithium diisopropyl amide In tetrahydrofuran Stage #2: prenyl bromide In tetrahydrofuran at 20℃;
  • 55
  • [ 781-35-1 ]
  • (S)-(-)-1,1-diphenylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In isopropyl alcohol at 20℃; for 17h;
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: Py / Heating 3: aq. KOH / methanol / Heating
  • 56
  • [ 781-35-1 ]
  • (R)-(+)-1,1-diphenylpropan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With carbonylhydridotris(triphenylphosphine)iridium(I); N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane In isopropyl alcohol at 75℃; for 8.5h;
93% With C38H38IrN4S2(1+)*F6P(1-); ammonium formate; 3-methyl-5-p-methoxyphenyl-1-hydropyrazole In tetrahydrofuran; water at 40℃; for 15h; enantioselective reaction;
68% With triiron dodecarbonyl; C52H58N4P2; hydrogen; potassium hydroxide In methanol at 45℃; for 10h; enantioselective reaction;
In isopropyl alcohol at 20℃; for 4h;
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: Py / Heating 3: aq. KOH / methanol / Heating
91 %Spectr. With bromopentacarbonylmanganese(I); C52H50N4P2; isopropyl alcohol; potassium hydroxide at 65℃; for 3h; Inert atmosphere; Schlenk technique; enantioselective reaction; 2. Typical procedure for ATH of ketones General procedure: Chiral ligands were synthesized using the procedure we previously reported.1-3 Under a nitrogen atmosphere, the complex [MnBr(CO)5] (2.7 mg, 0.01 mmol), (R,R,R',R')-CyP2N4 (L5) (8.0 mg, 0.01 mmol) were placed in a schlenk tube equipped with a Teflon-coated magnetic stirring bar. Then, iPrOH was added and the mixture was stirred at 55 oC for 30 min. Next, an appropriate amount of KOH/iPrOH solution was added, and the mixture was continually stirred for another 15 min. Later, ketone (0.5 mmol) was introduced, and the mixture was stirred at the desired temperature for the required reaction time. At the end of experiment, 1,3,5-trimethoxybenzene (28.0 mg,0.1667 mmol) as an internal standard was added, the reaction products were determined by GC using a chiralCP-Chiralsil-Dex CB column. Yields were determined by 1H NMR analysis of the crude reaction mixture.

  • 57
  • [ 22875-82-7 ]
  • [ 781-35-1 ]
  • [ 2042-85-5 ]
YieldReaction ConditionsOperation in experiment
1: 9% 2: 87% With gallium(III) trichloride; methyl cyclohexane In 1,2-dichloro-ethane at 80℃; for 1h;
  • 58
  • [ 781-35-1 ]
  • [ 4124-41-8 ]
  • [ 849943-94-8 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 1,1-diphenylacetone With potassium <i>tert</i>-butylate In tetrahydrofuran at -20 - 0℃; for 1.66667h; Inert atmosphere; Stage #2: p-toluenesulfonylanhydride In tetrahydrofuran at -20 - 0℃; for 6h; Inert atmosphere; 3.1 General procedure for the synthesis of alkenyl tosylate 1a-1i, 1k-1l General procedure: The solution of ketone or aldehyde (ca. 3 mmol) in THF (10 mL) was cooled to -20 °C. 1.0 M t-BuOK in THF (1.1-1.5 equiv) was added dropwise to the solution over 10 min. The mixture was warmed to 0 °C, stirred for 1.5 h, and then cooled to -20 °C. p-Toluenesulfonic anhydride (1.1-1.5 equiv) was added to the solution and the mixture was stirred for 1 h, then warmed to 0 °C, and stirred for 5 h. The mixture was diluted with EtOAc, washed with H2O and brine, dried over MgSO4, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (SiO2, hexane/EtOAc 30/1-10/1) to afford the desired alkenyl tosylate.
75% Stage #1: 1,1-diphenylacetone With sodium t-butanolate In tetrahydrofuran at -20 - 20℃; for 1.5h; Inert atmosphere; Stage #2: p-toluenesulfonylanhydride In tetrahydrofuran at -15 - -5℃; for 1.5h; Inert atmosphere;
75% Stage #1: 1,1-diphenylacetone With sodium t-butanolate In tetrahydrofuran at -20 - 20℃; Inert atmosphere; Stage #2: p-toluenesulfonylanhydride In tetrahydrofuran at -15 - -5℃; for 1.5h; Inert atmosphere;
73% Stage #1: 1,1-diphenylacetone With sodium t-butanolate In 1-methyl-pyrrolidin-2-one at -5 - 20℃; for 1.25h; Stage #2: p-toluenesulfonylanhydride In 1-methyl-pyrrolidin-2-one at -15 - -5℃; for 1h;

  • 59
  • [ 781-35-1 ]
  • [ 71713-10-5 ]
  • 6,6'-bis(2-(diphenylmethylene)-4-phenylquinoline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With diphenyl hydrogen phosphate In toluene at 120℃; for 24h;
  • 60
  • [ 781-35-1 ]
  • [ 109-77-3 ]
  • 2-methyl-3,3-diphenylprop-1-ene-1,1-dicarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With aluminum oxide at 60℃; for 1h; 3.2. Preparation of 1a A mixture of 1,1-diphenylacetone (1.051 g, 5.0 mmol), malononitrile (0.330 g, 5.0 mmol) and activated alumina (1.5 g) was stirred at 60 C for 1 h [34]. The solids were removed by filtration. Concentration of the filtrate gave a residue that was subjected to silica gel column chromatography followed by recrystallization from hexane to give 2-(1,1-diphenylpropan-2-ylidene)malononitrile (1a, white solid, 0.531 g, 2.06 mmol, 41% yield). Lit [35].
32.3% With piperidine; ammonium acetate; acetic acid In benzene for 15h; Heating;
27% With acetic acid In benzene Heating;
  • 61
  • [ 108-86-1 ]
  • [ 1833-53-0 ]
  • [ 781-35-1 ]
  • [ 103-79-7 ]
YieldReaction ConditionsOperation in experiment
With manganese(II) fluoride; zinc(II) fluoride; tri-tert-butyl phosphine In N,N-dimethyl-formamide at 70℃;
  • 62
  • [ 781-35-1 ]
  • [ 4757-69-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaOAc; NH2OH*HCl / methanol; H2O / 4 h / 20 °C 2: 75 mg / DIAD; tri-n-butylphosphine / acetonitrile / 2 h / 20 °C 3: 89 percent / o-xylene / 16 h / 150 °C
Multi-step reaction with 4 steps 1: trifluoroacetic acid / benzene / 4 h / Reflux 2: 13 h / 40 °C 3: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 4: Ni(1,5-cyclooctadiene)2; tricyclopentylphosphine / toluene / 12 h / 80 °C
  • 63
  • [ 781-35-1 ]
  • [ 65817-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaOAc; NH2OH*HCl / methanol; H2O / 4 h / 20 °C 2: 75 mg / DIAD; tri-n-butylphosphine / acetonitrile / 2 h / 20 °C
Multi-step reaction with 3 steps 1: 86 percent / AcOH, NaOAc / ethanol / 24 h / Heating 2: 16 h / Ambient temperature 3: 55 percent / NaH / dimethylsulfoxide / 4 h / Ambient temperature
Multi-step reaction with 3 steps 1: trifluoroacetic acid / benzene / 4 h / Reflux 2: 13 h / 40 °C 3: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / methanol / 120 °C 2: dichloromethane / 60 °C 3: caesium carbonate / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid / ethanol / 36 h / Reflux 2: 4 h / 40 °C 3: sodium hydride / dimethyl sulfoxide / 2 h / 20 °C

  • 64
  • [ 781-35-1 ]
  • N-(2,2-diphenyl-1-methylethenyl)formamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: t-BuONa / 1-methyl-pyrrolidin-2-one / 1.25 h / -5 - 20 °C 1.2: 73 percent / 1-methyl-pyrrolidin-2-one / 1 h / -15 - -5 °C 2.1: 91 percent / K3PO4; dipf / Pd2dba3 / 2-methyl-butan-2-ol / 20 h / 100 °C
  • 65
  • [ 781-35-1 ]
  • N-(2,2-diphenyl-1-methylethenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: t-BuONa / 1-methyl-pyrrolidin-2-one / 1.25 h / -5 - 20 °C 1.2: 73 percent / 1-methyl-pyrrolidin-2-one / 1 h / -15 - -5 °C 2.1: 96 percent / K3PO4; dipf / Pd2dba3 / 2-methyl-butan-2-ol / 20 h / 100 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 2 h / 0 °C 1.2: 75 percent / tetrahydrofuran / 0 - 20 °C 2.1: 76 percent / Cs2CO3; Xantphos / Pd2(dba)3 / dioxane / 20 h / 80 °C
  • 66
  • [ 781-35-1 ]
  • [ 412335-94-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C 1.2: 81 percent / tetrahydrofuran / 20 °C 2.1: 86 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 67
  • [ 781-35-1 ]
  • [ 167300-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 59 percent / tetrahydrofuran / 20 °C 2.1: 84 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 68
  • [ 781-35-1 ]
  • 2-methyl-5,5-diphenyltetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 59 percent / tetrahydrofuran / 20 °C 2.1: 84 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 90 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 70 °C
  • 69
  • [ 781-35-1 ]
  • 4,4-diphenyl-2-propyltetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 23 percent / tetrahydrofuran 2.1: 79 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 47 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 64 h / 70 °C
  • 70
  • [ 781-35-1 ]
  • [ 752206-82-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 92 percent / tetrahydrofuran / 20 °C 2.1: 62 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 71
  • [ 781-35-1 ]
  • 2,2-dimethyl-5,5-diphenyltetrahydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 17 percent / tetrahydrofuran / 20 °C 2.1: 87 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 50 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 70 °C
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 92 percent / tetrahydrofuran / 20 °C 2.1: 62 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 98 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 80 °C
  • 72
  • [ 781-35-1 ]
  • [ 752206-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 96 percent / tetrahydrofuran / 20 °C 2.1: 57 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 73
  • [ 781-35-1 ]
  • (Z)-2,2-diphenyl-4-hepten-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 23 percent / tetrahydrofuran 2.1: 79 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 74
  • [ 781-35-1 ]
  • 2,2-diphenyl-5-methyl-5-hexen-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 17 percent / tetrahydrofuran / 20 °C 2.1: 87 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 75
  • [ 781-35-1 ]
  • rac-(3aR,7aR)-3,3-Diphenyloctahydrobenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 96 percent / tetrahydrofuran / 20 °C 2.1: 57 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 87 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 70 °C
  • 76
  • [ 781-35-1 ]
  • 3,3-diphenyl-1-oxa-spiro[4.5]decane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran 1.2: 76 percent / tetrahydrofuran / 20 °C 2.1: 87 percent / LiAlH4 / tetrahydrofuran / 20 °C 3.1: 98 percent / P(4-C6H4CF3)3 / [PtCl2(CH2=CH2)]2 / 1,1,2,2-tetrachloro-ethane / 70 °C
  • 77
  • [ 781-35-1 ]
  • [ 752206-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran 1.2: 76 percent / tetrahydrofuran / 20 °C 2.1: 87 percent / LiAlH4 / tetrahydrofuran / 20 °C
  • 78
  • [ 781-35-1 ]
  • [ 4528-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / t-BuOK / various solvent(s) / 20 °C 2: PTSA / toluene 3: Red-Al / toluene / 0 - 20 °C
Multi-step reaction with 3 steps 1: 92 percent / potassium tert-butoxide / diethyl ether / 18 h / Ambient temperature 2: 32 percent / KOH-H2O / tetrahydrofuran; diethyl ether; various solvent(s) / 18 h / Ambient temperature 3: 61 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / Heating
Multi-step reaction with 3 steps 1: 92 percent / potassium tert-butoxide / diethyl ether / 18 h / Ambient temperature 2: 80 percent / p-TsOH / benzene / 0.5 h / Heating 3: 61 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / Heating
  • 79
  • [ 781-35-1 ]
  • 2-methoxy-2,5-dimethyl-5-(1,1-diphenylmethyl)-Δ3-1,3,4-oxadiazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73 percent / acetic acid / ethanol / 24 h / Heating 2: 63 percent / lead tetraacetate
  • 80
  • [ 781-35-1 ]
  • [ 143300-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 73 percent / acetic acid / ethanol / 24 h / Heating 2: 63 percent / lead tetraacetate 3: 50 percent / CHCl3 / 6 h / Ambient temperature; Irradiation
  • 81
  • [ 781-35-1 ]
  • [ 118318-10-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: t-BuOK / 1.) tert-butyl alcohol, reflux, 30 min; 2.) 60 deg C, 1 h 2: 40 percent / diethyl ether; benzene / 1 h / Ambient temperature 3: 62.5 percent / POCl3, pyridine / 3.5 h / 80 °C
  • 82
  • [ 781-35-1 ]
  • [ 118318-13-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: t-BuOK / 1.) tert-butyl alcohol, reflux, 30 min; 2.) 60 deg C, 1 h 2: 40 percent / diethyl ether; benzene / 1 h / Ambient temperature 3: 62.5 percent / POCl3, pyridine / 3.5 h / 80 °C 4: 84.4 percent / Li, NH3(liquid) / tetrahydrofuran / 0.08 h / -78 °C
  • 83
  • [ 781-35-1 ]
  • [ 118318-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: t-BuOK / 1.) tert-butyl alcohol, reflux, 30 min; 2.) 60 deg C, 1 h 2: 40 percent / diethyl ether; benzene / 1 h / Ambient temperature
  • 84
  • 2,2-diphenyl-1,1a,2,2a-tetrahydro-7H-cyclobut<a>inden-1-one [ No CAS ]
  • [ 781-35-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 92 percent / diethyl ether / 3 h 2: DCNB / Irradiation
  • 85
  • [ 781-35-1 ]
  • [ 4571-02-2 ]
YieldReaction ConditionsOperation in experiment
98.54% With oxygen; sodium hydroxide; sodium sulfite In ethanol at 15℃; for 6h; 18 Example 18 Synthesis of 1-hydroxy-1,1-diphenylacetone To a 250 ml three-necked flask was added sodium hydroxide (8 g, 0.2 mol) and ethanol (150 ml) at 15 ° C,0.5h. Followed by the addition of sodium sulfite (25.21 g, 0.2 mol), 1,1-diphenylacetone (42.05 g, 0.2 mol)1000ml size of the oxygen balloon, stirring reaction 6h.After completion of the reaction, the pH of the reaction solution was adjusted to 7 with 2M hydrochloric acid, and ethanol was distilled off under reduced pressure. Add 50 ml of water to(30 ml x 3), the combined organic phase was dried over anhydrous Na2SO4, and the mixture was partitioned with toluene. The solvent was evaporated to dryness to give 45.50 g of a pale yellow solid, 98% purity and 98.54% yield.
82% Stage #1: 1,1-diphenylacetone With sulfuric acid; sodium dodecyl-sulfate In water at 60℃; Stage #2: With iodine In water at 60℃; Stage #3: With sodium nitrite In water at 60℃; regioselective reaction;
53% With oxygen; caesium carbonate; triethyl phosphite In dimethyl sulfoxide at 25℃; for 24h; Schlenk technique; regioselective reaction;
53% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; dimethyl sulfoxide at 25℃; for 24h; Schlenk technique;
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: aqueous dioxane
Multi-step reaction with 2 steps 1: tetrachloromethane; carbon dioxide; bromine 2: BaCO3; water

  • 86
  • [ 781-35-1 ]
  • [ 6000-59-5 ]
  • C17 H14 N2 O C [ No CAS ]
  • [ 172937-96-1 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate In 1,2-dimethoxyethane 7 Preparation 7 Preparation 7 A solution of 1,1-diphenylacetone (25 g) and glyoxylic acid monohydrate (41.6 g) in 1,2-dimethoxyethane (75 ml) was refluxed for 3 days. The solution was partitioned between ethyl acetate and water. The organic layer was washed with water (twice) and evaporated in vacuo. The residue was partitioned between ethyl acetate and ammonia solution (200 ml) and the aqueous layer was separated. To the aqueous layer was added hydrazine hydrate (22.6 g) and the mixture was stirred for 2 hours at 100° C. After being cooled, the reaction mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 6-diphenylmethyl-3(2H)-pyridazinone (6.26 g) as a white powder. mp: 161°-162° C. IR (Nujol) 3300-2800, 1660, 1600, 760, 740, 700 cm-1 NMR (CDCl3, δ): 5.44 (1H, s), 6.88 (1H, d, J=9.8 Hz), 7.10-7.40 (11H, m), 11.29 (1H, br s) MASS (+APCI): 263 (M+ +1) Elemental Analysis Calcd. for C17 H14 N2 O C 77.84, H 5.38, N 10.68 Found C 77.76, H 5.39, N 10.66
  • 87
  • [ 505-18-0 ]
  • [ 781-35-1 ]
  • [ 14171-36-9 ]
  • 1,1-diphenyl-3-piperidin-2-yl-propan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With hydrogenchloride In <i>N</i>-methyl-acetamide IX 1,1-Diphenyl-3-(2-piperidyl)propan-2-one EXAMPLE IX 1,1-Diphenyl-3-(2-piperidyl)propan-2-one Magnesium methyl carbonate (1.2 moles, 2 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 1,1-diphenylacetone, 63.0 g (0.3 moles), is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen to form the chelate, allowing the methyl alcohol that forms to escape. The mixture is cooled to room temperature under an atmosphere of carbon dioxide and 30.0 g (0.36 moles) of 2,3,4,5-tetrahydropyridine (as α-tripiperidein) is added and stirring continued at room temperature for a period of 6 days under an atmosphere of carbon dioxide. The reaction mixture is poured into 375 ml of concentrated HCl on 400 g of ice and the resulting mixture is extracted with methylene dichloride. The extracts are combined, dried over anhydrous sodium sulfate and the solvent is removed. The crude oil is recrystallized twice from an aqueous isopropyl alcohol solution to yield 37.9 g (37% yield) of 1,1-diphenyl-3-(2-piperidyl)propan- 2-one as the hydrochloride salt having a M.P. of 197-9°C. (dec.)
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