Morpholine → HCID 13044301, compound

HRID 434685Notes

Reaction equation

HRID 434685 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.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.CN(C)P(=O)(N(C)C)N(C)C>C(OCC)(=O)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:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 12679HexamethylphosphoramideHCID 13472993HCID 13472993, compound

Product 1

HCID 13044301HCID 13044301, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 200 ml stainless steel autoclave were placed 10 g of 9-fluoro-8-bromo-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 12.8 g of morpholine and 80 ml of hexamethylphosphoric triamide and the mixture was reacted at 160° C. on an oil bath. After 7 hours, the temperature of the autoclave was lowered to room temperature and disappearance of the starting materials was confirmed by thin layer chromatography. Then, the reaction mixture was transferred from the autoclave to a 300 ml Erlenmeyer flask to which ethyl acetate was added and the resulting mixture was allowed to stand for 1 day. The crystals which formed were collected by filtration and recrystallized from dimethylformamide to give 4 g of 9-fluoro-8-morpholino-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. m.p. 279°-280° C., white rhombic crystals.

Workup

  1. customthe mixture was reacted at 160° C. on an oil bath
  2. customwas lowered to room temperature
  3. additionwas added
  4. waitto stand for 1 day
  5. customThe crystals which formed
  6. filtrationwere collected by filtration
  7. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-4abffd42f3104e84a470431753777bc6
Source dataset
uspto-grants-1983_08
Patent number
US04399134

Reaction notes

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