Water → HCID 21994084, compound

HRID 1978402Notes

Reaction equation

HRID 1978402 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12](=[O:25])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(OC(N1CCNC(=O)C1)=O)(C)(C)C.BrCCCC1C=CC=CC=1.O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12](=[O:25])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 12503(3-Bromopropyl)benzeneHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 23682953HCID 23682953, compound

Product 1

HCID 21994084HCID 21994084, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthesis of 4-tert-Butoxycarbonyl-1-(3-phenylpropan-1-yl)-2-oxopiperazine Sodium hydride (60% in oil, 630 mg, 15.8 mmol) was added to a stirred solution of 4-tert-butoxycarbonyl-2-oxopiperazine (3.00 g, 15.0 mmol) in N,N-dimethylformamide (40 ml) at room temperature and the stirring was continued at room temperature for 30 minutes. 1-Bromo-3-phenylpropane (3.29 g, 16.5 mmol) was added to the mixture and the stirring was continued 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 (50 g) with hexane-ethyl acetate (1:1) to give 4-tert-butoxycarbonyl-1-(3-phenylpropan-1-yl)-2-oxopiperazine as colorless crystals (3.85 g, 81%), which were collected by filtration and washed with hexane.

Workup

  1. waitthe stirring was continued 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 (50 g) with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-080e3e6ab0ad452d86d6212336dfdb01
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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