4-Methylpiperidine → HCID 13044287, compound

HRID 1583612Notes

Reaction equation

HRID 1583612 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][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]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:25]1[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 13472993HCID 13472993, compound

Product 1

HCID 13044287HCID 13044287, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

In a 100 ml flask were placed 7 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 10.2 g of 4-methylpiperidine and 60 ml of hexamethylphosphoric triamide and the mixture was stirred at 160° C. in nitrogen gas atmosphere. After 6.5 hours, disappearance of the starting materials was confirmed by thin layer chromatography, and hexamethylphosphoric triamide was removed using a vacuum pump. To the residue was added several drops of concentrated hydrochloric acid and then ethyl acetate to separate oily substances from crystals. The crystals were collected by filtration and recrystallized from dimethylformamide-water to give 200 mg of 9-fluoro-8-(4-methyl-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 266° to 268° C., white rhombic crystals.

Workup

  1. customIn a 100 ml flask were placed
  2. customwas removed
  3. additionTo the residue was added several drops of concentrated hydrochloric acid
  4. customethyl acetate to separate oily substances from crystals
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-7e9252eca8e94266ab9b0000e7752662
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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