Water → 2-(4-Benzylpiperazin-2-yl)ethan-1-ol

HRID 1035322Notes

Reaction equation

HRID 1035322 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=O)[NH:11][C@H:10]([CH2:15][C:16](OCC)=[O:17])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH2:15][CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 91665637HCID 91665637, compound

Product 1

HCID 468394992-(4-Benzylpiperazin-2-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Example 255D (9.2 g, 33.3 mmol) in tetrahydrofuran (150 mL) at 0° C. was added lithium aluminum hydride (2 M, tetrahydrofuran, 50 mL) dropwise. The solution was allowed to warm to room temperature and stirred for 16 hours. Water (3.8 mL) in tetrahydrofuran (25 mL) was added dropwise to the solution followed by 3.8 mL NaOH (15% aqueous) and more water (11.4 mL). The solids were removed via filtration. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound.

Workup

  1. customThe solids were removed via filtration
  2. customPurification via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d1d47afd1173432dbf7f62c8c5112bbd
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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