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

HRID 1973951Notes

Reaction equation

HRID 1973951 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[OH-].[Na+].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1>O>[CH3:8][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1=[N:1][C:20]([NH:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([F:11])([F:22])[F:23])=[CH:18][CH:17]=1)=[O:21]

Participants

5

Reactant 3

HCID 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 962WaterSolvent

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 K 2 CO 3, 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 recrystallizations 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 K 2 CO 3
  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
  8. customrecrystallizations of the solid from methanol

Sources & evidence

ORD record
ord-5e1c00514d9c49e095df92622460ecad
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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