Ammonia → 1,2-Dihydro-6-methyl-2-oxo-5-[4-(4-phenyl-1-piperidinyl)phenyl]-3-pyridine carbonitrile

HRID 2164272Notes

Reaction equation

HRID 2164272 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]([NH2:11])=O)=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CN(C)C=O.N>O>[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:11])=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 14812Phosphorus oxide (P4O10)HCID 133942421,2-Dihydro-6-methyl-2-oxo-5-[4-(4-phenyl-1-piperidinyl)phenyl]-3-pyridinecarboxamide

Product 1

HCID 204060631,2-Dihydro-6-methyl-2-oxo-5-[4-(4-phenyl-1-piperidinyl)phenyl]-3-pyridine carbonitrileYield 12.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.9 g (0.00232 mole) of 1,2-dihydro-6-methyl-2-oxo-5-[4-(4-phenyl-1-piperidinyl)phenyl]-3-pyridinecarboxamide, 1.8 g of P2O5, and 10 ml of dimethylformamide was refluxed for one hour, cooled to room temperature, and poured into 100 ml of water. The solution was adjusted to pH 6.7 with NH3 and the solid collected. After recrystallizing twice from MeOH (using charcoal treatment), 105 mg of a light brown solid was obtained. Approximately 80 mg of this solid was stirred overnight in 5 ml of saturated NaHCO3 (to which two drops of MeOH were added), then it was collected, washed, and dried. Sixty one mg of light brown solid was obtained.

Workup

  1. temperaturewas refluxed for one hour
  2. customthe solid collected
  3. customAfter recrystallizing twice from MeOH (using charcoal treatment)

Sources & evidence

ORD record
ord-6d4f53381f404551b0987d9632f31588
Source dataset
uspto-grants-1985_03
Patent number
US04503061

Reaction notes

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