1-(2-Methyl-5-nitro-phenyl)-piperidin-4-one → 3-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)piperidin-4-one

HRID 1853945

Reaction equation

HRID 1853945 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1>COC(OC)N(C)C>[CH3:3][N:11]([CH:16]=[C:13]1[C:14](=[O:17])[CH2:15][CH2:16][N:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:12]1)[CH3:12]

Participants

3

Reactant 1

HCID 666567781-(2-Methyl-5-nitro-phenyl)-piperidin-4-one

Product 1

HCID 673288983-Dimethylaminomethylene-1-(2-methyl-5-nitrophenyl)piperidin-4-one

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 1-(2-Methyl-5-nitro-phenyl)-piperidin-4-one [100 mg, 0.426 mmol] in N,N-Dimethylformamide dimethyl acetal (DMA.DMF) [1 ml] was heated to reflux for 12 hrs. After cooling to room temperature, reaction mixture was concentrated under vacuum. The dark brown crude product obtained was further purified by silica gel chromatography using 30-60% ethyl acetate/hexane as eluent to obtain pure desired product i.e., 3-Dimethylaminomethylene-1-(2-methyl-5-nitro-phenyl)-piperidin-4-one [4] as orange solid [Yield: 76.2 mg, 62.02%]

Workup

  1. temperatureto reflux for 12 hrs
  2. customreaction mixture
  3. concentrationwas concentrated under vacuum
  4. customThe dark brown crude product obtained
  5. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2b4d79805b2495988cffa207aa2cc19
Source dataset
uspto-grants-2015_02
Patent number
US08962637B2

Linked notes

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