Water → HCID 9886269, compound

HRID 1384844Notes

Reaction equation

HRID 1384844 reaction equation
Cl.[S:2]1[CH:6]=[C:5]([C:7](=[O:24])[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:12][CH2:11]2)[C:4]2[CH:25]=[CH:26][CH:27]=[CH:28][C:3]1=2.[BH4-].[Na+].O>CO>[S:2]1[CH:6]=[C:5]([CH:7]([OH:24])[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:12][CH2:11]2)[C:4]2[CH:25]=[CH:26][CH:27]=[CH:28][C:3]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21183867HCID 21183867, compound

Product 1

HCID 9886269HCID 9886269, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 500 mg of 1-(benzo[b]thiophen-3-yl)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-one hydrochloride (1.20×10−3 moles) in 30 ml of MeOH a 0° C. was added NaBH4 for about 20 min until the reaction ceased to evolve. After two hours 50 ml of H2O were added to the medium, it was stirred for a few minutes and was extracted twice with 200 ml of AcOEt. The organic phase was washed three times with H2O, was dried with Na2SO4 and the solvent was removed. It was purified in silica column with AcOEt/hexane (1:1). The free base was thus obtained in form of a white solid. Yield: 30%. Two polymorphic forms of this product were obtained, the melting points of which were 108° C. and 120° C. respectively.

Workup

  1. extractionwas extracted twice with 200 ml of AcOEt
  2. washThe organic phase was washed three times with H2O
  3. dry with materialwas dried with Na2SO4
  4. customthe solvent was removed
  5. customIt was purified in silica column with AcOEt/hexane (1:1)
  6. customThe free base was thus obtained in form of a white solid
  7. customTwo polymorphic forms of this product were obtained
  8. customwere 108° C. and 120° C.

Sources & evidence

ORD record
ord-c51329dfaee64d01b356f7c0487c639a
Source dataset
uspto-grants-2001_07
Patent number
US06262056B1

Reaction notes

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