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

HRID 364943
Notes
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Reaction equation

HRID 364943 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-1c02fd06bcaf4135acca892d38c0671b
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04607037

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes