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Chemical Structure| 21363-69-9 Chemical Structure| 21363-69-9

Structure of 21363-69-9

Chemical Structure| 21363-69-9

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Product Details of [ 21363-69-9 ]

CAS No. :21363-69-9
Formula : C16H19NO3
M.W : 273.33
SMILES Code : O=C(OCC)C=C1CCN(C(C2=CC=CC=C2)=O)CC1

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Application In Synthesis of [ 21363-69-9 ]

* 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 [ 21363-69-9 ]

[ 21363-69-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 867-13-0 ]
  • [ 24686-78-0 ]
  • [ 21363-69-9 ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane; ice-water; mineral oil; EXAMPLE 1 Preparation of N-acetyl-4-piperidineacetaldehyde A 55 percent dispersion of sodium hydride in mineral oil containing 3.24 g. of a 55percent dispersion of sodium hydride in mineral oil was washed with three 50 ml portions of dry pentane and then the sodium hydride was suspended in 100 ml of anhydrous 1,2-dimethoxyethane (to be referred to hereinafter as DME). 16.58 g. of triethylphosphonoacetate in 50 ml of anhydrous DME were added to the sodium hydride suspension under a nitrogen atmosphere slowly with stirring and cooling to about 0° C. After the addition had been completed, the ice bath was removed and the mixture stirred for an additional hour at ambient temperature. The ice bath was then replaced and a solution of 10 g. of N-benzoyl-4-piperidone in 25 ml of anhydrous DME was added in dropwise fashion with stirring. After this addition had been completed, the ice bath was again removed and stirring continued for about three hours. Excess solvents were removed in vacuo from the reaction mixture. About 100 ml of an ice-water mixture were added. The resulting aqueous mixture was extracted with three 100 ml portions of ether, and the ether extracts separated, combined and dried. Removal of the ether therefrom in vacuo yielded a residue comprising N-benzoyl-4-(carbethoxymethylene) piperidine formed in the above reaction. Recrystallization of the residue from hexane yielded about 11.7 g. of colorless prisms of N-benzoyl-4-(carbethoxymethylene) piperidine melting at about 102°-103° C. N-benzoyl-4-(carbethoxymethylene) piperidine thus prepared had the following physical characteristics. Boiling point = 178°-180° C. at 0.03 mm Hg. nmr (CDCL3): delta1.28 (5, 3), 2.38 (broad m, 2), 3.05 (broad m, 2), 3.67 (broad m, 4), 4.18 (q, 2), 5.78 (broad s, 1), 7.41 (s,5). ir (KBr): 1715, 1660, 1620 cm-1. Anal: Calcd. for C16 H19 NO3: C, 70.31; H, 7.01; N, 5.13. Found: C, 70.42; H, 7.10; N, 5.07.
  • 2
  • [ 24686-78-0 ]
  • [ 1099-45-2 ]
  • [ 21363-69-9 ]
YieldReaction ConditionsOperation in experiment
92% In toluene; for 2h;Heating / reflux; Preparation of 30.3:A mixture of 30.1 (10.2 g, 0.050 mol, 1.0 eq) and 30.2 (25 g, 0.075 mol, 1.5 eq) in toluene (100 mL) under nitrogen was refluxed for 2h. The mixture was concentrated under reduced pressure and the crude product was purified by column chromatography (eluent: hexane/ethyl acetate, 1:1). Yield: 92percent1H NMR (400MHz, CDCl3) delta 7.42 (s, 5H), 5.78 (brs, IH), 3.83 (brs, 2H), 3.70 (s, 3H), 3.49 (brs, 2H), 3.02 (brm, 2H), 2.37 (brm, 2H) Mass Spectral Analysis m/z = 259.9 (MH-H)+
 

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