Water → 1-(1-Methyl-2-piperidylidene)-3-(4-trifluoromethylphenyl)urea

HRID 2071523Notes

Reaction equation

HRID 2071523 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[OH-].[Na+].O.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>CO>[CH3:8][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[N:1][C:21]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:23])[F:24])=[CH:19][CH:18]=1)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 124490281-Methylpiperidin-2-imine

Product 1

HCID 542292351-(1-Methyl-2-piperidylidene)-3-(4-trifluoromethylphenyl)urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpiperidine (7.60 g.; 0.068 mole) is converted to free base by adding 7 ml. of NaOH (50%) to an aqueous slurry (using a minimal amount of water) of the salt and then extracting with benzene. After drying over K2CO3, the benzene solution is filtered through diatomaceous earth. A benzene solution of 12.73 g. (0.068 mole) of p-trifluoromethylphenylisocyanate [prepared according to Inukai and Maki, Kogyo Kagaku Zasshi, 67 (5) 807-9 (1964] is added to the above solution slowly. After 4 hours of stirring at room temperature, the benzene is evaporated in vacuo to give a solid residue. Repeated recrystallizatons of the solid from methanol yields the pure product, 1-(1-methyl-2-piperidylidene)-3-(4-trifluoromethylphenyl)urea, m.p. = 154°-155° C.

Workup

  1. additionby adding 7 ml
  2. extractionextracting with benzene
  3. dry with materialAfter drying over K2CO3
  4. filtrationthe benzene solution is filtered through diatomaceous earth
  5. additionis added to the above solution slowly
  6. customthe benzene is evaporated in vacuo
  7. customto give a solid residue

Sources & evidence

ORD record
ord-cc533664f58a47ee956e181f1746cd86
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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