1-(4-Methoxy-benzyl)-4-(4-nitro-phenyl)-piperidine-2,6-dione → 4-(4-Nitrophenyl)piperidine-2,6-dione

HRID 930133Notes

Reaction equation

HRID 930133 reaction equation
COC1C=CC(C[N:8]2[C:13](=[O:14])[CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[CH2:10][C:9]2=[O:24])=CC=1>CC#N.O>[N+:21]([C:18]1[CH:17]=[CH:16][C:15]([CH:11]2[CH2:10][C:9](=[O:24])[NH:8][C:13](=[O:14])[CH2:12]2)=[CH:20][CH:19]=1)([O-:23])=[O:22]

Participants

4

Reactant 1

HCID 597711911-(4-Methoxy-benzyl)-4-(4-nitro-phenyl)-piperidine-2,6-dione

Product 1

HCID 534263034-(4-Nitrophenyl)piperidine-2,6-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A suspension of 22.8 g (64.2 mmol) of 1-(4-methoxy-benzyl)-4-(4-nitro-phenyl)-piperidine-2,6-dione (as prepared in the previous step) in CH3CN (150 mL) was treated with 70.4 g (128 mmol) of ceric ammonium nitrate (CAN) as a solution in water (100 mL). The mixture was stirred at RT for 5 h, diluted with water (100 mL), and extracted with EtOAc (2×150 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (1×100 mL) and water (1×100 mL). The combined aqueous layers were extracted with EtOAc (1×100 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The solid residue was triturated with a minimum amount of CH3CN, filtered, and air-dried. The filtrate was concentrated and triturated again with a minimum amount of CH3CN, filtered, and air-dried as a second batch. The two batches were combined to afford 7.00 g (47%) as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 8.26 (d, 2H, J=8.8 Hz), 7.97 (br s, 1H), 7.42 (d, 2H, J=8.8 Hz), 3.62-3.52 (m, 1H), 3.02-2.93 (m, 2H), 2.84-2.74 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 (1×100 mL) and water (1×100 mL)
  3. extractionThe combined aqueous layers were extracted with EtOAc (1×100 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe solid residue was triturated with a minimum amount of CH3CN
  7. filtrationfiltered
  8. customair-dried
  9. concentrationThe filtrate was concentrated
  10. customtriturated again with a minimum amount of CH3CN
  11. filtrationfiltered
  12. customair-dried as a second batch
  13. customto afford 7.00 g (47%) as an off-white solid

Sources & evidence

ORD record
ord-9aad23e1bb1d4f399838279b731278c7
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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