Acetate → HCID 13044299, compound

HRID 1583622Notes

Reaction equation

HRID 1583622 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-d1f9d53d552943f08d037c5fc1c7f285
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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