HCID 69088302, compound → HCID 69032357, compound

HRID 2251847Notes

Reaction equation

HRID 2251847 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])=[C:8]([NH:10][C:11](=[O:19])[CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:9]=1)([O-])=O>CCO.O1CCOCC1>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:20]([CH3:23])([CH3:22])[CH3:21])=[C:8]([NH:10][C:11](=[O:19])[CH2:12][N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[CH:9]=1

Participants

4

Reactant 1

HCID 69088302HCID 69088302, compound

Product 1

HCID 69032357HCID 69032357, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(5-Nitro-2-tert-butylpheny)-2-piperidin-1-yl-acetamide (1.77 g, 5.5 mmol) was dissolved in EtOH (100 mL) and 1,4-dioxane (10 mL). The solution was degassed under vacuum with stirring. A catalytic amount of 5% Pd/C was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (balloon) and stirred overnight at RT. The reaction was filtered through Celite® with MeOH and the filtrate was concentrated under reduced pressure. The recovered material was eluted through a column of silica gel with a 5 to 40% (90:10:1 CH2Cl2:MeOH:NH4OH(aq)) to CH2Cl2 linear gradient giving a brown foamy solid. MS: 290 (M+1). Calc'd. for C17H27N3O—289.42.

Workup

  1. customThe solution was degassed under vacuum
  2. additionA catalytic amount of 5% Pd/C was added (as a slurry in EtOH)
  3. customThe mixture was degassed again
  4. additionthe reaction vessel was charged with H2 gas (balloon)
  5. stirringstirred overnight at RT
  6. filtrationThe reaction was filtered through Celite® with MeOH
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe recovered material was eluted through a column of silica gel with a 5 to 40% (90:10:1 CH2Cl2:MeOH:NH4OH(aq)) to CH2Cl2 linear gradient
  9. customgiving a brown foamy solid

Sources & evidence

ORD record
ord-4d68cc192b834a6bb0c75c64d39cc6e3
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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