Sodium Hydroxide → HCID 57964191, compound

HRID 2403525Notes

Reaction equation

HRID 2403525 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25](OCC)=[O:26])[CH:20]=4)[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH2:17][CH2:18]3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 68811174HCID 68811174, compound

Product 1

HCID 57964191HCID 57964191, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a cooled solution of 2.5 g (6.25 mmol) of 1-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]-4-(3-ethoxycarbonylphenyl)piperazine (prepared by path II), is added, under argon, 0.36 g (9.36 mmol) of lithium aluminum hydride. The suspension is stirred overnight at room temperature. Hydrolysis is performed at 0° C. by slow addition of 0.35 mL of water, 0.35 mL of 15% aqueous sodium hydroxide solution and 1.0 mL of water. The slurry is stirred for 15 minutes at room temperature then magnesium sulfate is added. The mixture is filtered and the salts are washed with ethyl acetate. The filtrate is concentrated under reduced pressure to give 2.0 g (89%) of 1-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethyl]-4-(3-hydroxymethylphenyl)piperazine as a solid.

Workup

  1. customHydrolysis
  2. stirringThe slurry is stirred for 15 minutes at room temperature
  3. filtrationThe mixture is filtered
  4. washthe salts are washed with ethyl acetate
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-5090ef274b664bfaa19fe32d42c4daaa
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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