Water → 4-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)butan-1-ol

HRID 655640Notes

Reaction equation

HRID 655640 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:29]3[CH:28]=[CH:27][S:26][C:25]=3[CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)(=O)C.O>CO>[S:26]1[CH:27]=[CH:28][C:29]2[C:21]([N:18]3[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][CH2:12][CH2:11][OH:10])[CH2:20][CH2:19]3)=[CH:22][CH:23]=[CH:24][C:25]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 574825494-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate

Product 1

HCID 574825504-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)butan-1-olYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (3.87 g, 28 mmol) was added to a solution of 7.76 g (23.3 mmol) of 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate in 90% methanol solution (150 ml). The solution mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, which was then extracted with dichloromethane. The extraction solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1), and concentrated under reduced pressure to obtain 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butan-1-ol (6.65 g) as colorless oil.

Workup

  1. extractionwas then extracted with dichloromethane
  2. dry with materialThe extraction solution was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fd77a1034c249b18aa8a661e0416deb
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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