Tetrahydrofuran → 3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propanol

HRID 655638Notes

Reaction equation

HRID 655638 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH2:18][CH2:17]3)=[CH:13][CH:14]=[CH:15][C:8]1=2.O1CCCC1.[OH-].[Na+]>O>[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([N:16]3[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:20][CH2:21]3)=[CH:13][CH:14]=[CH:15][C:8]1=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57482547Ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate

Product 1

HCID 574825483-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propanolYield 5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium aluminum hydride (1.18 g, 24.8 mmol) was added to a solution of 5.26 g (16.5 mmol) of ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate in a tetrahydrofuran (THF) solution (55 ml) under ice cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction solution, water (1.2 ml), 15% aqueous sodium hydroxide solution (1.2 ml), and water (3.6 ml) were added in this order and the mixture was stirred at room temperature. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate) and concentrated to dryness under reduced pressure to obtain 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propan-1-ol (0.23 g) as white powder.

Workup

  1. stirringthe mixture was stirred at room temperature
  2. customInsoluble matter was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate)
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-703fbf2958744f0ea467833afb1d0b3b
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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