Diisopropylethylamine → HCID 28963661, compound

HRID 2370633Notes

Reaction equation

HRID 2370633 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][OH:12].C(N(C(C)C)CC)(C)C.[CH3:22][N:23]1[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(#N)C>[CH3:22][N:23]1[CH2:29][CH2:28][CH2:27][N:26]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH2:11][OH:12])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 28963661HCID 28963661, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2-fluoro-5-nitrophenyl)methanol (4.500 g, 26.3 mmol), diisopropylethylamine (6.89 mL, 39.4 mmol), and 1-methyl-1,4-diazepane (4.25 mL, 34.2 mmol) in acetonitrile (150 mL) was refluxed for 24 hours. The solvent was evaporated. The residue was treated with saturated aqueous NaHCO3 and extracted with ethyl acetate (twice). The combined organic layers were dried over MgSO4 and filtered. The title compound was crystallized from the organic layers.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe solvent was evaporated
  3. additionThe residue was treated with saturated aqueous NaHCO3
  4. extractionextracted with ethyl acetate (twice)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customThe title compound was crystallized from the organic layers

Sources & evidence

ORD record
ord-51e80df9a8cd4faeada1a5733e735e3d
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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