Piperidine → HCID 13669719, compound

HRID 1982404Notes

Reaction equation

HRID 1982404 reaction equation
I[CH2:2][CH:3]1[O:22][C:6]2[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]3[C:13]([C:14](=[O:15])[C:5]=2[CH2:4]1)=[CH:12][CH:11]=[CH:10][N:9]=3.N1CCCCC1>>[CH2:2]=[C:3]1[O:22][C:6]2[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]3[C:13]([C:14](=[O:15])[C:5]=2[CH2:4]1)=[CH:12][CH:11]=[CH:10][N:9]=3

Participants

3

Reactant 2

HCID 8082PiperidineHCID 13669715HCID 13669715, compound

Product 1

HCID 13669719HCID 13669719, compound

Procedure

A solution of 2 g. of 3,9-dihydro-2-(iodomethyl)-9-phenyl-furo(2,3-b)-1,8-naphthyridin-4(2H)-one in 4 g. of dry piperidine is stirred at room temperature for 72 hours. The reaction mixture is diluted with 80 ml. of water, filtered and the solids washed well with water. The aqueous filtrate is made strongly basic with sodium hydroxide solution and filtered. The combined solids are purified on a grade 62 silica gel column using 5 pts MeOH, 95 pts ethyl acetate as solvent. Fraction III is triturated with 2×50 ml. of hot isopropyl ether yielding the title compound, m.p. 259°-261° C.

Workup

  1. additionThe reaction mixture is diluted with 80 ml
  2. filtrationof water, filtered
  3. washthe solids washed well with water
  4. filtrationfiltered
  5. customThe combined solids are purified on a grade 62 silica gel column
  6. customFraction III is triturated with 2×50 ml

Sources & evidence

ORD record
ord-4a2c1481b8ec44e08f36819c4941c876
Source dataset
uspto-grants-1986_06
Patent number
US04596809

Reaction notes

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