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

HRID 1500554Notes

Reaction equation

HRID 1500554 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.O.[OH-].[Na+]>O1CCCC1>[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 962Water2×HCID 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 8028TetrahydrofuranSolvent

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 tetrahydrofuran (55 ml) with cooling in an ice-bath, followed by stirring at room temperature for 4 hours. Water (1.2 ml), 15% sodium hydroxide aqueous solution (1.2 ml), and water (3.6 ml) were added to the reaction mixture in this order with stirring at room temperature. Insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate), then concentrated and dried under reduced pressure to obtain 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propane-1-ol (0.23 g) as white powder.

Workup

  1. temperaturewith cooling in an ice-bath
  2. stirringwith stirring at room temperature
  3. customInsoluble matters were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate)
  6. concentrationconcentrated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3aefa2bf87b14e90ba6659421f522c04
Source dataset
uspto-grants-2015_12
Patent number
US09206167B2

Reaction notes

Loading…