Piperidine → HCID 13044288, compound

HRID 434682Notes

Reaction equation

HRID 434682 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1Br.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C)P(=O)(N(C)C)N(C)C>[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 13472993HCID 13472993, compound

Product 1

HCID 13044288HCID 13044288, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
160 °C

Procedure

In a 200 ml autoclave were placed 5 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 5 g of piperidine and 45 ml of hexamethylphosphoric triamide and the mixture was stirred at 160° C. After 5.5 hours, the temperature was lowered to room temperature and disappearance of the starting materials was confirmed by thin layer chromatography followed by removing hexamethylphosphoric triamide using a vacuum pump (120° C./2 mm Hg). To the residue was added several drops of concentrated hydrochloric acid and then ethyl acetate. Crystals which formed were collected by filtration and washed with ethyl acetate. The crystals thus obtained were recrystallized from dimethylformamide-water and the resulting crystals were added sodium hydroxide and water so as to obtain an aqueous solution of pH 13 which then was treated with activated carbon and filtered. The filtrate was adjusted to pH 7 with acetic acid to precipitate crystals which then were collected by filtration and recrystallized from dimethylformamide-water to give 570 mg of 9-fluoro-8-(1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 258°-261° C., white rhombic crystals.

Workup

  1. customwas lowered to room temperature
  2. customby removing hexamethylphosphoric triamide using a vacuum pump (120° C./2 mm Hg)
  3. additionTo the residue was added several drops of concentrated hydrochloric acid
  4. customCrystals which formed
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate
  7. customThe crystals thus obtained
  8. customwere recrystallized from dimethylformamide-water
  9. additionthe resulting crystals were added sodium hydroxide and water so as
  10. customto obtain an aqueous solution of pH 13 which
  11. additionthen was treated with activated carbon
  12. filtrationfiltered
  13. customto precipitate crystals which
  14. filtrationthen were collected by filtration
  15. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-262a2d86fc7c4e9da6286c2c65494469
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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