4-Methylpiperidine → HCID 13044287, compound

HRID 434681Notes

Reaction equation

HRID 434681 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-a2635ec2ff0c47e39955b9db922c4c6f
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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