Diisopropylethylamine → HCID 66783136, compound

HRID 1096269Notes

Reaction equation

HRID 1096269 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][NH:4][C:3]1=[O:8].F[C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:1][CH:2]1[N:7]([C:10]2[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:15]=2)[CH2:6][CH2:5][NH:4][C:3]1=[O:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 51066003-Methyl-2-ketopiperazine

Product 1

HCID 66783136HCID 66783136, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-methyl-2-ketopiperazine (200 mg, 1.75 mmol), 5-fluoro-2-nitrobenzo-trifluoride (366 mg, 1.75 mmol), N,N-diisopropylethylamine and N,N-dimethylformamide (1 mL) was heated at 140° C. for 10 min under microwave irradiation, then partitioned between sat. aq. ammonium chloride solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 4:1) produced the title compound (130 mg, 24%). Yellow solid, MS: 304.1 (M+H)+.

Workup

  1. custompartitioned between sat. aq. ammonium chloride solution and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9b70964d591f447797649896ba74d67b
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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