Water → 3-(2-(4-(3-chloro-2-methylphenyl)-1-piperazinyl)ethyl)-5,6-dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazole

HRID 2258467Notes

Reaction equation

HRID 2258467 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=1)[N:7]=[C:6]2[CH2:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=2[CH3:41])[CH2:30][CH2:29]1)=O.O1CCCC1.B.O>O1CCCC1>[Cl:40][C:36]1[C:35]([CH3:41])=[C:34]([N:31]2[CH2:32][CH2:33][N:28]([CH2:26][CH2:25][C:6]3[C:5]4[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=4)[N:7]=3)[CH2:29][CH2:30]2)[CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 155123151-((5,6-Dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazol-3-yl)acetyl)-4-(3-chloro-2-methylphenyl)piperazine

Product 1

HCID 99159363-(2-(4-(3-chloro-2-methylphenyl)-1-piperazinyl)ethyl)-5,6-dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazoleYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-((5,6-Dimethoxy-1-(3,4-dimethoxybenzyl)-1H-indazol-3-yl)acetyl)-4-(3-chloro-2-methylphenyl)piperazine (60.5 g) was suspended in tetrahydrofuran (1000 ml). Then 1.0 mol-borane tetrahydrofuran complex tetrahydrofuran solution (500 ml) was added thereto and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled to room temperature and water (30 ml) was added to thereby decompose the excessive reagent. After evaporation of the tetrahydrofuran under reduced pressure, conc. hydrochloric acid (300 ml) was added and the mixture was stirred at 50° C. for 1 hour. The aqueous layer was returned to room temperature and made alkaline with potassium carbonate. Then it was extracted with chloroform (3000 ml) and the organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue thus obtained was purified by using a silica gel column (chloroform/ethanol=40/1). Thus a colorless solid (50.0 g) was obtained. This product was recrystallized from ethanol to give 46.3 g of colorless prism crystals (m.p.: 148°-150° C.)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of the tetrahydrofuran under reduced pressure, conc. hydrochloric acid (300 ml)
  4. additionwas added
  5. customwas returned to room temperature
  6. extractionThen it was extracted with chloroform (3000 ml)
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified

Sources & evidence

ORD record
ord-3978a85c961542939e445cf54b8776c3
Source dataset
uspto-grants-1997_08
Patent number
US05661150

Reaction notes

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