1-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine → 1-{3-[Bis(4-hydroxyphenyl)methyl]indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine

HRID 442852Notes

Reaction equation

HRID 442852 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:36]2[CH:41]=[CH:40][C:39]([O:42]COC)=[CH:38][CH:37]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:25][CH2:24]2)=[O:22])=[CH:7][CH:6]=1>O1CCCC1.C(O)C.Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:36]2[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[CH2:27][CH2:28]2)=[O:22])=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 158589011-{3-{Bis[4-(methoxymethoxy)phenyl]methyl}indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazine

Product 1

HCID 701554591-{3-[Bis(4-hydroxyphenyl)methyl]indol-2-ylcarbonyl}-4-(2-chlorophenyl)piperazineYield 89.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 1 (1.43 g, 2.28 mmol) obtained in Example 1 was dissolved in a mixed solvent of tetrahydrofuran (20 ml) and ethanol (20 ml), and 5 ml of 2N hydrochloric acid was added thereto, followed by heating under reflux for 0.5 hours. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium bicarbonate was added thereto followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate, and the solvent was distilled off under pressure. The resulting residue was washed with diethyl ether/ethyl acetate and crystallized to give 1.1 g (yield: 88%) of the title compound.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 0.5 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. additiona saturated aqueous solution of sodium bicarbonate was added
  6. extractionthereto followed by extraction with ethyl acetate
  7. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was distilled off under pressure
  10. washThe resulting residue was washed with diethyl ether/ethyl acetate
  11. customcrystallized

Sources & evidence

ORD record
ord-9d4f6a7c81754419985d1cc925bd6b0c
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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