Water → HCID 57423909, compound

HRID 2064064Notes

Reaction equation

HRID 2064064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.O.C(OCC)(=O)C>CN(C)C=O.C(N(C(C)C)CC)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 57423909HCID 57423909, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-2-fluoronitrobenzene (3.5 g) was dissolved in dry dimethylformamide (25 mL) and diisopropylethylamine (3.6 mL), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (4.2 g) were added at room temperature. The mixture was stirred at 80° C. for 1 h, then cooled to room temperature and water and ethyl acetate added. The organic layer was dried over MgSO4, filtered and evaporated, and the residue was purified by chromatography eluting with 10 to 25% ethyl acetate in hexane to afford the title compound, 6.8 g.

Workup

  1. temperaturecooled to room temperature
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was purified by chromatography
  6. washeluting with 10 to 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4accc71d8bd24ba390096157ec0131a1
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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