4-Acetamidopiperidine → HCID 13044297, compound

HRID 434689Notes

Reaction equation

HRID 434689 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]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)(=[O:23])[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:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:21](=[O:23])[CH3:22])[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 14451564-AcetamidopiperidineHCID 13472993HCID 13472993, compound

Product 1

HCID 13044297HCID 13044297, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Conditions

Temperature
150 °C

Procedure

A mixture of 3.5 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 6 g of 4-acetylaminopiperidine and 30 ml of hexamethylphosphoric triamide was heated at 150° C. for 4 hours. After completion of reaction, hexamethylphosphoric triamide was distilled off under reduced pressure, and the residue was recrystallized from dimethylformamide-water. Crystals which formed were again recrystallized from dimethylformamide to give 0.82 g of 9-fluoro-8-(4-acetylamino-1-piperidyl)-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 274°-277° C., white rhombic crystals.

Workup

  1. distillationwas distilled off under reduced pressure
  2. customthe residue was recrystallized from dimethylformamide-water
  3. customCrystals which formed
  4. customwere again recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-3f64897171f04ae6acec912a6df20079
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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