Sodium sulfate decahydrate → HCID 19043493, compound

HRID 1683330Notes

Reaction equation

HRID 1683330 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][N:4]1[C:9](=O)[CH2:8][C:7]([CH3:12])([CH3:11])[CH2:6][C:5]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:1][CH:2]([CH3:14])[CH2:3][N:4]1[CH2:5][CH2:6][C:7]([CH3:11])([CH3:12])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 19043494HCID 19043494, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19043493HCID 19043493, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of N-(2-Methylpropyl)-3,3-dimethylglutarimide (19.5 g, 0.0984 mol) in dry ether (30 ml) was added via a dropping funnel over 30 minutes to a suspension of lithium aluminum hydride (5.36 g, 0.141 mol) in dry ether (50 ml) at 0° C. stirring under nitrogen. The mixture was then boiled for 3 hours, allowed to cool to room temperature and the excess lithium aluminium hydride was decomposed by careful addition of solid sodium sulphate decahydrate (20 g). After the suspended solid had turned white, the mixture was filtered, the solid washed twice with ether (2×50 ml), and the combined filtrate concentrated to yield a colourless liquid. Distillation gave the pure product, (1-(2-methylpropyl)-4,4-dimethylpipeidine, 13.0 g (82%), b.p. 81°-82° C./16 mmHg. 1H NMR (CDCl 3) δ2.30 (4H, t), 2.05 (2H, d), 1.80 (1H, m), 1.35 (4H, t), 0.90 (6H, s) and 0.85 (6H, d).

Workup

  1. filtrationthe mixture was filtered
  2. washthe solid washed twice with ether (2×50 ml)
  3. concentrationthe combined filtrate concentrated
  4. customto yield a colourless liquid
  5. distillationDistillation
  6. customgave the pure product

Sources & evidence

ORD record
ord-782608b4493d456a96841db90cf4e53a
Source dataset
uspto-grants-1997_06
Patent number
US05637718

Reaction notes

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