Piperidine → HCID 20258995, compound

HRID 1583611Notes

Reaction equation

HRID 1583611 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[C:19]2=[C:20]3[N:15]([CH:16]([CH3:21])[CH2:17][CH2:18]2)[CH:14]=[C:13]([C:22](=[O:24])[CH3:23])[C:12](=[O:25])[C:11]3=[CH:10][C:9]=1[F:26]>CN(C)P(=O)(N(C)C)N(C)C>[N:1]1([C:8]2[C:19]3=[C:20]4[N:15]([CH:16]([CH3:21])[CH2:17][CH2:18]3)[CH:14]=[C:13]([C:22](=[O:24])[CH3:23])[C:12](=[O:25])[C:11]4=[CH:10][C:9]=2[F:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082Piperidine2×HCID 20258998HCID 20258998, compound

Product 1

HCID 20258995HCID 20258995, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Anhydrous piperidine (8 g) was added to 5.3 g of 8-chloro-9-fluoro-5-methyl-2-acetyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine. 70 ml of hexamethylphosphoric triamide was added thereto and the mixture was allowed to react at 140° C. on an oil bath for 6 hours. After completion of the reaction any excess solvent and piperidine were removed by distillation under reduced pressure and 100 ml of ethyl acetate was added to the residue to precipitate light yellow crystals. The crystals thus obtained were separated by filtration and 300 ml of water was added thereto followed by adjusting the resulting solution to a pH of 2 with 1N hydrochloric acid. The solution was heated and filtered. The filtrate was concentrated to 50 ml and rendered alkaline with a 10% aqueous sodium hydroxide solution to obtain 3.0 g of 8-(1-piperidyl)-9-fluoro-5-methyl-2-acetyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine.

Workup

  1. customto react at 140° C. on an oil bath for 6 hours
  2. customwere removed by distillation under reduced pressure and 100 ml of ethyl acetate
  3. additionwas added to the residue
  4. customto precipitate light yellow crystals
  5. customThe crystals thus obtained
  6. customwere separated by filtration and 300 ml of water
  7. additionwas added
  8. temperatureThe solution was heated
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated to 50 ml

Sources & evidence

ORD record
ord-92a35f24f62040b492780a96e9bca7be
Source dataset
uspto-grants-1985_11
Patent number
US04552879

Reaction notes

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