Piperidine → HCID 67392724, compound

HRID 1851665Notes

Reaction equation

HRID 1851665 reaction equation
[N:1]1([C:6]([O:8][CH2:9][CH2:10][C:11]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:26])[C:13]=3[CH:12]=2)=[O:7])[CH:5]=[CH:4]N=[CH:2]1.N1CCC[CH2:29][CH2:28]1>CN(C)C=O>[N:1]1([C:6]([O:8][CH2:9][CH2:10][C:11]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:26])[C:13]=3[CH:12]=2)=[O:7])[CH2:2][CH2:29][CH2:28][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 67391885HCID 67391885, compound

Product 1

HCID 67392724HCID 67392724, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution dissolved 12.1 g of N,N′-carbonyldiimidazole (75 mmol; produced by Wako Pure Chemical Industries, Ltd) into 50 mL of dehydrated dimethylformamide (dehydrated DMF), 15.8 g of 2-anthraquinonyl-1-ethylalcohol (62 mmol) obtained by the same method as Synthetic Example 5 was added, then, the solution was reacted by stirring for 1 hour at room temperature. After completing reaction, ice-water was poured into the reaction solution, and this mixed solution was extracted with toluene, and further after organic layer after extraction was washed with water, the organic layer was condensed. The resultant condensed residue was purified with column chromatography (Filler: Silica-gel (Wako-gel C-200; produced by Wako Pure Chemical Industries, Ltd.), Developing solvent: ethyl acetate/n-heptane=1/9) to obtain 12.3 g of 2-anthraquinonyl-1-ethyl 1-imidazolylcarboxylate (yield: 57%) as yellow crystal. Subsequently, to the solution dissolved the resultant crystal of 2-anthraquinonyl-1-ethyl 1-imidazolylcarboxylate into 50 mL of dehydrated dimethylformamide (dehydrated DMF), 4.2 g of piperidine (50 mmol) was added, then, the solution was reacted for 1 hour at room temperature. After completing reaction, ice-water was poured into the reaction solution, this mixed solution was extracted with toluene, and further, organic layer after extraction was washed with water, the organic layer was condensed. The resultant condensed residue was purified with column chromatography (Filler: Silica-Gel (Wako-Gel C-200; produced by Wako Pure Chemical Industries, Ltd.), Developing solvent: ethyl acetate/n-heptane=1/9) to obtain 9.8 g of 2-anthraquinonyl-1-ethyl piperidinecarboxylate (yield: 43%) represented by the above-described formula [12] as yellow crystal. Measurement results of 1H-NMR and melting point are shown as the follows:

Workup

  1. additionwas added
  2. customthe solution was reacted for 1 hour at room temperature
  3. additionwas poured into the reaction solution
  4. extractionthis mixed solution was extracted with toluene
  5. extractionfurther, organic layer after extraction
  6. washwas washed with water
  7. customcondensed
  8. customThe resultant condensed residue
  9. customwas purified with column chromatography (Filler: Silica-Gel (Wako-Gel C-200; produced by Wako Pure Chemical Industries, Ltd.), Developing solvent: ethyl acetate/n-heptane=1/9)

Sources & evidence

ORD record
ord-f04ea8f2904540819f3e2512429bf2a4
Source dataset
uspto-grants-2015_02
Patent number
US08957212B2

Reaction notes

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