Water → HCID 66881150, compound

HRID 541958Notes

Reaction equation

HRID 541958 reaction equation
Cl.Cl.[Br:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH3:19][Si:20]([CH3:35])([CH3:34])[CH2:21][CH2:22][O:23][C:24](ON1C(=O)CCC1=O)=[O:25].O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][N:16]([C:24]([O:23][CH2:22][CH2:21][Si:20]([CH3:35])([CH3:34])[CH3:19])=[O:25])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 66880938HCID 66880938, compound

Product 1

HCID 66881150HCID 66881150, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1-(2-bromo-4-nitrophenyl)piperazine dihydrochloride (1.9 g, 5.8 mmol) in acetonitrile (50 mL) was treated with 1-({[2-(trimethylsilyl)ethoxy]carbonyl}oxy)pyrrolidine-2,5-dione (1.5 g, 5.9 mmol) followed by water (15 mL) and sodium carbonate (1.9 g, 18 mmol) and stirred at 20° C. for 6 h. The reaction mixture was diluted with ethyl acetate (400 mL) and washed with water and brine, dried over anhydrous sodium sulfate, filtered, and evaporated to give a residue. This material was purified by flash column chromatography to give the desired product (2.4 g, 87%) as a solid. [TEOC: (2-(trimethylsilyl)ethoxy)carbonyl]

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give a residue
  6. customThis material was purified by flash column chromatography

Sources & evidence

ORD record
ord-cd5be3b1aa0e485abb11740d08b97f21
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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