Sodium hydride → 1-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]piperazine

HRID 2083942Notes

Reaction equation

HRID 2083942 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=CC=CC=1.[H-].[Na+].[CH3:16][C:17]1([CH3:34])[O:21]C(COS(C2C=CC(C)=CC=2)(=O)=O)C[O:18]1>CN(C)C=O>[CH3:16][C:17]1([CH3:34])[O:21][CH:2]([CH2:1][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH2:7][O:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 759941-BenzylpiperazineHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

Product 1

HCID 227322391-[(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.6 ml N-benzylpiperazine in dimethylformamide (30 ml) is treated slowly with sodium hydride (510 mg). To this suspension is added toluene-4-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (0.8 g) and the mixture stirred overnight. The reaction mixture is evaporated, the residue is trated with water and the product extracted with ethyl acetate. The organic extract is dried and evaporated. The crude product is purified by flash chromatography on silica gel using heptane/ethyl acetate 1:1 as eluent. The purified intermediate (0.9 g) is dissolved in methanol (30 ml) and hydrogenated over palladium on charcoal (0.3 g). The catalyst is filtered off and the filtrate is evaporated to yield 0.54 g of the title compound as a waxy solid.

Workup

  1. customThe reaction mixture is evaporated
  2. extractionthe product extracted with ethyl acetate
  3. extractionThe organic extract
  4. customis dried
  5. customevaporated
  6. customThe crude product is purified by flash chromatography on silica gel
  7. dissolutionThe purified intermediate (0.9 g) is dissolved in methanol (30 ml) and hydrogenated over palladium on charcoal (0.3 g)
  8. filtrationThe catalyst is filtered off
  9. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-ada8aca96972430fb2ac5802def8536f
Source dataset
uspto-grants-2004_04
Patent number
US06716845B2

Reaction notes

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