Dimethyl Sulfide → 218594-59-3

HRID 1972549Notes

Reaction equation

HRID 1972549 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][CH:7]1[NH:12][C:11](=O)[CH2:10][NH:9][C:8]1=O.C1COCC1.CSC>[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][CH:7]1[CH2:8][NH:9][CH2:10][CH2:11][NH:12]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8028TetrahydrofuranHCID 223429193-(3-Methoxybenzyl)-2,5-piperazinedione

Product 1

HCID 22342893218594-59-3Yield 85.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

To a 100-mL round-bottomed flask was added 3-(3-methoxybenzyl)-2,5-piperazinedione (201 mg, 0.858 mmol), 5 mL of THF and BH3.DMS (0.326 mL, 3.43 mmol, Aldrich, St. Louis, Mo.). The reaction mixture was stirred at 70° C. for 18 h and then diluted with 1N NaOH (12 mL) and extracted with CH2Cl2 (2×50 mL). The organic extracts were washed with saturated aqueous NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude 2-(3-methoxybenzyl)piperazine (152 mg) as a colorless tar.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe organic extracts were washed with saturated aqueous NaCl (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3abeda7c35f6410a9d1347564d2e1778
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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