Hydrogen Peroxide → HCID 57699525, compound

HRID 906354Notes

Reaction equation

HRID 906354 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)#[N:2].[OH-:23].[Na+].OO>CCO.O.[Na+].[Cl-]>[NH2:2][C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=[O:23]

Participants

7

Reactant 3

HCID 784Hydrogen Peroxide3×HCID 14798Sodium HydroxideHCID 576995121,1-Dimethylethyl 4-[(2-cyanophenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 57699525HCID 57699525, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 5234Sodium ChlorideSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(2-cyanophenyl)amino]-1-piperidinecarboxylate (D17) (355 mg, 1.18 mmol) in EtOH (6 ml) at 40° C. was added 2M NaOH solution (2.6 ml) followed by a mixture of hydrogen peroxide solution (27% w/w, 3.7 ml) in water (2.9 ml) and the reaction stirred for 2 h. Further hydrogen peroxide solution (27% w/w, 3.7 ml) in water (2.9 ml) was added and the reaction stirred at 40° C. for 1.5 h. Another portion of hydrogen peroxide solution (27% w/w, 7.4 ml) in water (5.8 ml) was added and stirring and heating were continued overnight. The reaction mixture was diluted with saturated aqueous NaCl solution (4 ml) and extracted with tBuOH (5 ml). The organic extract was diluted with EtOAc (15 ml), dried (MgSO4) and concentrated. Column chromatography eluting with 0-100% EtOAc/petroleum ether gave the title compound (150 mg). δH (CDCl3, 250 MHz) 7.96 (1H, br d), 7.40 (1H, m), 7.31 (1H, m), 6.71 (1H, d), 6.57 (1H, t), 5.80 (2H, br s), 3.93 (2H, m), 3.53 (1H, m), 3.06 (2H, m), 1.99 (2H, m), 1.50 (2H, m), 1.47 (9H, s). MS (ES): MH+ 320.

Workup

  1. stirringthe reaction stirred at 40° C. for 1.5 h
  2. stirringstirring
  3. temperatureheating
  4. waitwere continued overnight
  5. extractionextracted with tBuOH (5 ml)
  6. extractionThe organic extract
  7. additionwas diluted with EtOAc (15 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. washColumn chromatography eluting with 0-100% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-1eba68733e554c63b0918735b1213bed
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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