Potassium Carbonate → HCID 19602858, compound

HRID 1604327Notes

Reaction equation

HRID 1604327 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:10]([CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:19]=2)[CH:10]([CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19602919HCID 19602919, compound

Product 1

HCID 19602858HCID 19602858, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6 g (0.0205 mol) of 4-tert-butyloxycarbonyl-1-(4-hydroxyphenyl)-2-methylpiperazine, 2.4 ml (0.0246 mol) of methyl bromoacetate and 3.4 g (0.0246 mol) of potassium carbonate in 50 ml of dimethylformamide is heated at 100° C. for 6 hours and, after cooling, concentrated to dryness in vacuo. The residue is partitioned between ethyl acetate and water and the aqueous phase is extracted once more with ethyl acetate. The combined ethyl acetate extracts are concentrated to dryness in vacuo. The residue is purified by means of chromatography on a silica gel column, ethyl acetate/cyclohexane being used as eluent. After evaporation, the residue is crystallized from ether/petroleum ether.

Workup

  1. temperatureafter cooling
  2. concentrationconcentrated to dryness in vacuo
  3. customThe residue is partitioned between ethyl acetate and water
  4. extractionthe aqueous phase is extracted once more with ethyl acetate
  5. concentrationThe combined ethyl acetate extracts are concentrated to dryness in vacuo
  6. customThe residue is purified by means of chromatography on a silica gel column, ethyl acetate/cyclohexane being
  7. customAfter evaporation
  8. customthe residue is crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-0378a771828045aeb975c513bdd46afa
Source dataset
uspto-grants-1999_11
Patent number
US05994356

Reaction notes

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