Urea → 4-(4-Nitrophenyl)piperidine-2,6-dione

HRID 930123Notes

Reaction equation

HRID 930123 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:15][C:16]([OH:18])=O)[CH2:11][C:12](O)=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:19]C(N)=O>CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][C:16](=[O:18])[NH:19][C:12](=[O:13])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1176UreaHCID 184046303-(4-Nitrophenyl)pentanedioic acid

Product 1

HCID 534263034-(4-Nitrophenyl)piperidine-2,6-dioneYield 22.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 250 mg (0.987 mmol) of 3-(4-nitro-phenyl)-pentanedioic acid (as prepared in the previous step) and 119 mg (1.98 mmol) of urea was heated to 150° C. for 40 min (until all solid melted and gas evolution stopped). The mixture was cooled to RT, taken up in EtOAc (70 mL), washed with saturated aqueous NaHCO3 (2×40 mL), dried (MgSO4), and concentrated in vacuo to afford 52.0 mg (22%) of the title compound as a brown solid: 1H-NMR (CDCl3; 400 MHz): δ 8.28 (d, 2H, J=8.8 Hz), 7.44 (d, 2H, J=8.8 Hz), 3.64-3.54 (m, 1H), 3.04-2.96 (m, 2H), 2.86-2.76 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with saturated aqueous NaHCO3 (2×40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f04bb1568f1346e58d6ea6ff77c28d09
Source dataset
uspto-grants-2016_03
Patent number
US09296726B2

Reaction notes

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