3-(Dimethylamino)phenol → HCID 9923791, compound

HRID 1071862Notes

Reaction equation

HRID 1071862 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH:11]1[C:16]([CH:17]=O)=[CH:15][C:14]2[O:19][CH2:20][O:21][C:13]=2[CH:12]=1.[C:22](#[N:26])[CH2:23][C:24]#[N:25].N1CCCCC1>C(O)C>[NH2:26][C:22]1[O:9][C:5]2[C:6]([CH:17]([C:16]3[CH:11]=[CH:12][C:13]4[O:21][CH2:20][O:19][C:14]=4[CH:15]=3)[C:23]=1[C:24]#[N:25])=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=2

Participants

6

Reactant 4

HCID 74213-(Dimethylamino)phenolHCID 8010MalononitrileHCID 8082PiperidineHCID 8438Piperonal

Product 1

HCID 9923791HCID 9923791, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-dimethylaminophenol (489 mg, 3.56 mmol), piperonal (535 mg, 3.56 mmol), and malononitrile (233 mg, 3.53 mmol) in ethanol (20 ml) was added piperidine (0.70 ml, 7.1 mmol). The mixture was stirred at room temperature for 2 h and the resulting solid was collected by filtration, washed with methanol and dried in vacuo to yield the title compound as a yellow solid (940 mg, 2.80 mmol, 79%). 1H NMR (DMSO-d6): 6.83-6.77 (m, 4H), 6.66-6.64 (m, 2H), 6.47-6.44 (m, 1H), 6.21 (s, 1H), 5.96 (s, 1H), 5.95 (s, 1H), 4.53 (s, 1H), 2.85 (s, 6H).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a55f285971a44cc085337aaf86db7250
Source dataset
uspto-grants-2005_06
Patent number
US06906203B1

Reaction notes

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