Water → HCID 23508733, compound

HRID 1883953Notes

Reaction equation

HRID 1883953 reaction equation
C(O[N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[CH:14][C:15]([OH:20])=[C:16]([CH:19]=2)[CH:17]=[O:18])[CH2:8][CH2:7]1)(C)(C)C.[C:21](=[O:24])([O-:23])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CN1C(=O)CCC1.C(OCC)(=O)C>[C:16]([O:23][C:21]([N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:13]=[CH:14][C:15]([O:20][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:16]([CH:17]=[O:18])[CH:19]=2)[CH2:10][CH2:11]1)=[O:24])([CH3:19])([CH3:17])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23508731HCID 23508731, compound

Product 1

HCID 23508733HCID 23508733, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.5 g of 5-(4-tert-butoxypiperazin-1-yl)-2-hydroxybenzaldehyde are dissolved in 5 ml of NMP at 20° under nitrogen with stirring, and 0.25 g of potassium carbonate and 0.2 ml of ethyl bromoacetate are added. The mixture is stirred at 110° for 30 minutes and cooled to 25°. 30 ml of water and 30 ml of ethyl acetate are added to the mixture, the phases are separated, and the aqueous phase is extracted with 30 ml of ethyl acetate. The combined organic phases are washed with 30 ml of water and freed from solvent under reduced pressure. 30 ml of toluene, 30 ml of water and 5 ml of 1N HCl are added to the crystal slurry which remains, the toluene phase is removed under reduced pressure, and the crystalline precipitate is separated off and dried at 40° under reduced pressure (0.48 g; 75%), m.p. 93-94° C.; MS 392 (M+), 336 (100%), 250/249, 57.

Workup

  1. stirringThe mixture is stirred at 110° for 30 minutes
  2. temperaturecooled to 25°
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with 30 ml of ethyl acetate
  5. washThe combined organic phases are washed with 30 ml of water
  6. addition30 ml of toluene, 30 ml of water and 5 ml of 1N HCl are added to the crystal slurry which
  7. customthe toluene phase is removed under reduced pressure
  8. customthe crystalline precipitate is separated off
  9. customdried at 40° under reduced pressure (0.48 g; 75%), m.p. 93-94° C.

Sources & evidence

ORD record
ord-cfb0370afb3243e5a35c1a30c975907b
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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