Ethyl Acetate → HCID 12853016, compound

HRID 1414391Notes

Reaction equation

HRID 1414391 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[C:16](=[O:27])[CH:17]=[C:18]([C:24](O)=[O:25])[O:19]2)[CH3:9].P(Br)(Br)Br.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:24]([C:18]2[O:19][C:20]3[C:15]([C:16](=[O:27])[CH:17]=2)=[C:14]([O:13][CH2:12][CH2:11][O:10][CH2:8][CH3:9])[CH:23]=[CH:22][CH:21]=3)=[O:25])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 531671-MethylpiperazineHCID 12769849HCID 12769849, compound

Product 1

HCID 12853016HCID 12853016, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-methylpiperazine (4.5g.) was added dropwise to a suspension of 5-(2-ethoxyethoxy)chromone-2-carboxylic acid (5.0g.) in chloroform (50ml.). A solution of phosphorus tribromide (2.0g.) in chloroform (10ml.) was added dropwise to the resultant mixture under ice cooling for 10 minutes. The mixture was stirred under ice cooling for 2 hours and at room temperature for additional 1 hour, and then ethyl acetate (250ml.) was added to the reaction mixture. The mixture was washed twice with 5% aqueous solution of sodium bicarbonate and with water in turn, and dried. The solvent was distilled off under reduced pressure to give 2-(4-methyl-1-piperazinyl)carbonyl-5-(2-ethoxyethoxy) chromone (500mg.). The product was derived in the usual manner to its maleate.

Workup

  1. washThe mixture was washed twice with 5% aqueous solution of sodium bicarbonate and with water in turn
  2. customdried
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-89b0ce1fe15e437b89c43a3c2514312c
Source dataset
uspto-grants-1977_01
Patent number
US04001280

Reaction notes

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