Acetate → HCID 13044299, compound

HRID 434691Notes

Reaction equation

HRID 434691 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.[C:21]([O-:24])(=O)[CH3:22]>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:8]1[CH2:9][CH2:22][C:21](=[O:24])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 175AcetateHCID 13472993HCID 13472993, compound

Product 1

HCID 13044299HCID 13044299, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of 3 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 5 g of 4-piperidineethylene acetate and 30 ml of hexamethylphosphoric triamide was heated at 160° C. on an oil bath for 6 hours. After completion of reaction, hexamethylphosphoric triamide was distilled off under reduced pressure, and to the residue was added ethyl acetate to precipitate crystals which then were recrystallized from dimethylformamide containing a small amount of dilute hydrochloric acid to give 0.87 g of 9-fluoro-8-(4-oxo-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. not lower than 300° C., white rhombic crystals.

Workup

  1. distillationwas distilled off under reduced pressure
  2. additionto the residue was added ethyl acetate
  3. customto precipitate crystals which
  4. customthen were recrystallized from dimethylformamide containing a small amount of dilute hydrochloric acid

Sources & evidence

ORD record
ord-f8842a62e14344bcb6397ee5e6722ab9
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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