Hydrogen Bromide → HCID 13044296, compound

HRID 1583619Notes

Reaction equation

HRID 1583619 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.[CH3:21][N:22]([CH3:29])[CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Br.Cl>O.[OH-].[Na+].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:26]1[CH2:27][CH2:28][CH:23]([N:22]([CH3:29])[CH3:21])[CH2:24][CH2:25]1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 417391N,N-Dimethylpiperidin-4-amineHCID 13472993HCID 13472993, compound

Product 1

HCID 13044296HCID 13044296, compoundYield 30.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 12 g of 4-dimethylaminopiperidine and 50 ml of hexamethylphosphoric triamide was heated at 150° C. on an oil bath for 5 hours. After completion of reaction, hexamethylphosphoric triamide was distilled off under reduced pressure and to the residue was added ethyl acetate to form crystals. The crystals were suspended in 500 ml of water and a 47% aqueous hydrobromic acid was added thereto to adjust pH to 3 followed by heating. Then, insoluble substances were removed by filtration. The filtrate was concentrated and the residue was recrystallized from ethanol-water. Crystals which formed were dissolved in a 10% aqueous sodium hydroxide solution and the resulting solution was adjusted to pH 8 with dilute hydrochloric acid to precipitate white crystals, which then were dried to give 2.4 g of 9-fluoro-8-(4-dimethylamino-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 259°-261° C., white rhombic crystals. T1 -Elemental Analysis for C21H26O3N3F? -C? H? N? -Calc'd (%): 65.10 6.76 10.85 -Found (%): 64.97 6.88 10.72 -

Workup

  1. distillationwas distilled off under reduced pressure and to the residue
  2. additionwas added ethyl acetate
  3. customto form crystals
  4. temperatureby heating
  5. customThen, insoluble substances were removed by filtration
  6. concentrationThe filtrate was concentrated
  7. customthe residue was recrystallized from ethanol-water
  8. customCrystals which formed
  9. customto precipitate white crystals, which
  10. customthen were dried

Sources & evidence

ORD record
ord-8240ac7457e24d97b2b544a8c51f5e8c
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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