Water → 1,1-Dimethylethyl 4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-3-oxo-1-piperazinecarboxylate

HRID 1978389Notes

Reaction equation

HRID 1978389 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[O:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][CH2:20][N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[C:12](=[O:16])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 219938971,1-Dimethylethyl 4-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-3-oxo-1-piperazinecarboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 1.78 g, 44.5 mmol) was added in a small portions to a stirred solution of 4-tert-butoxycarbonyl-2-oxopiperazine (8.00 g, 40.0 mmol) in N,N-dimethylformamide (100 ml) at room temperature and the mixture was stirred at room temperature for 1 hour. Then, N-(3-bromopropyl)phthalimide (12.5 g, 46.6 mmol) was added to the mixture. After stirring at room temperature for 1 hour, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was successively washed with water, brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (150 g) with hexane-ehtyl acetate (1:1) to give 4-tert-butoxycarbonyl-1-(3-phthalimidopropan-1-yl)-2-oxopiperazine as a colorless oil (9.02 g, 55%).

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was successively washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (150 g) with hexane-ehtyl acetate (1:1)

Sources & evidence

ORD record
ord-7c5ac3d2b6a24130a37e066189360e33
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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