Sodium hydride → 4-Benzyloxycarbonyl-1-(p-methoxybenzyl)-piperazin-2-one

HRID 1436507Notes

Reaction equation

HRID 1436507 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 736777Benzyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 690157874-Benzyloxycarbonyl-1-(p-methoxybenzyl)-piperazin-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to a solution of 4-benzyloxycarbonyl-piperazin-2-one (2 g, 8.6 mmol) in dry THF (10 mL/mmol) under nitrogen, sodium hydride (236 mg, 9.4 mmol, 60% dispersion in mineral oil) in one portion and stir at room temperature for 30 min. Add p-methoxybenzyl chloride (1.86 mL, 13 mmol) and stir at room temperature overnight. Concentrate, add ethyl acetate, wash with water, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate) to give the title compound as an oil (1.6 g, 54%).

Workup

  1. concentrationConcentrate
  2. additionadd ethyl acetate
  3. washwash with water, saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-474dca69fe854402817812a0ea1ea0c7
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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