Diisopropylethylamine → HCID 59850185, compound

HRID 2064148Notes

Reaction equation

HRID 2064148 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](F)[CH:3]=1.C(N(C(C)C)CC)(C)C.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1>CN(C)C=O>[F:8][C:7]1[C:2]([Br:1])=[CH:3][C:4]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 27362864-Bromo-2,5-difluoronitrobenzene

Product 1

HCID 59850185HCID 59850185, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-2,5-difluoronitrobenzene (0.60 g, 2.5 mmole) was dissolved in dry dimethylformamide (10 ml) and diisopropylethylamine (0.39 g, 3.0 mmole), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.53 g, 2.6 mmole) were added at room temperature and subsequently stirred for 1 hour. The mixture was then stirred at 80° C. for 2.5 h, then cooled to room temperature. The mixture was concentrated to dryness under vacuum and the residue partitioned between ethyl acetate and dilute aqueous potassium carbonate solution. The organic layer was dried over MgSO4, filtered and evaporated, and the residue was purified by silica gel chromatography eluting with 10 to 50% diethyl ether in 40-60 pet ether to afford the title compound as an orange/red solid, 0.91 g, 87%. LC/MS—97% m/e-416/418 (M−H).

Workup

  1. stirringThe mixture was then stirred at 80° C. for 2.5 h
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. customthe residue partitioned between ethyl acetate and dilute aqueous potassium carbonate solution
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 10 to 50% diethyl ether in 40-60 pet ether

Sources & evidence

ORD record
ord-bdc30e587ffc423ea4949036b61612b3
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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