Water → HCID 23508727, compound

HRID 1883950Notes

Reaction equation

HRID 1883950 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([CH:21]=2)[CH:19]=[O:20])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].O>CN1C(=O)CCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:22][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:18]([CH:19]=[O:20])[CH:21]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23508725HCID 23508725, compound

Product 1

HCID 23508727HCID 23508727, compoundYield 70%

Reagents, catalysts & solvents 2

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

Procedure

0.5 g of 5-(4-benzylpiperazin-1-yl)-2-hydroxybenzaldehyde are dissolved in 5 ml of NMP at 20° C. 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 4 hours and cooled to 15°. 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. Combined organic phases are washed with 2×30 ml of water and freed from solvent under reduced pressure. The yellow oil which remains (0.7 g) is chromatographed on 10 g of silica gel (MTB ether/heptane 5:1) and gives 0.45 g of product (70%; yellowish oil), MS 382 (M+), 296, 263, 199, 149, 119, 91 (100%).

Workup

  1. stirringThe mixture is stirred at 110° for 4 hours
  2. temperaturecooled to 15°
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with 30 ml of ethyl acetate
  5. washCombined organic phases are washed with 2×30 ml of water
  6. customis chromatographed on 10 g of silica gel (MTB ether/heptane 5:1)

Sources & evidence

ORD record
ord-06e47b654cc74f35804b29e882dd34e0
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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