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

HRID 1907362Notes

Reaction equation

HRID 1907362 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→3 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→3 ethyl acetate)
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7c5266e03d744ff0b89bd870524ec459
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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