Hexane → 3-[Bis(4-hydroxyphenyl)methyl]-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indole

HRID 442869Notes

Reaction equation

HRID 442869 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:37]2[CH:42]=[CH:41][C:40]([O:43]COC)=[CH:39][CH:38]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[S:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[CH2:26][CH2:25]2)(=[O:23])=[O:22])=[CH:7][CH:6]=1.CCCCCC>O1CCCC1.C(O)C.Cl>[OH:43][C:40]1[CH:39]=[CH:38][C:37]([CH:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[S:21]([N:24]2[CH2:25][CH2:26][N:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[CH2:28][CH2:29]2)(=[O:22])=[O:23])=[CH:42][CH:41]=1

Participants

6

Reactant 2

HCID 8058HexaneHCID 676918923-(Bis[4-(methoxymethoxy)phenyl]methyl)-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indole

Product 1

HCID 675942623-[Bis(4-hydroxyphenyl)methyl]-2-[4-(2-chlorophenyl)piperazinylsulfonyl]indoleYield 89%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 241 (1.0 g, 1.51 mmol) obtained in Example 242 was dissolved in a mixed solvent of tetrahydrofuran (10 ml) and ethanol (30 ml), and 20 ml of 2N hydrochloric acid was added thereto, followed by heating under reflux for 2 hours. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium bicarbonate was added thereto for neutralization. The mixture was stirred and the precipitated crystals were collected to give a crude product. The obtained crude product was washed with ethanol and a little amount of hexane to give 0.77 g (yield: 89%) of the title compound.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 2 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. additiona saturated aqueous solution of sodium bicarbonate was added
  6. customthe precipitated crystals were collected
  7. customto give a crude product
  8. customThe obtained crude product
  9. washwas washed with ethanol

Sources & evidence

ORD record
ord-96f5ac3eb9fa415eaa7ec1e499aad32d
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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