Water → 1-Phenyl-3-(1-methyl-2-piperidylidene)urea

HRID 1973950Notes

Reaction equation

HRID 1973950 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[OH-].[Na+].O.[C:12]1([N:18]=[C:19]=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1C=CC=CC=1>[C:12]1([NH:18][C:19]([N:1]=[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][N:3]2[CH3:8])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 124490281-Methylpiperidin-2-imine

Product 1

HCID 540801711-Phenyl-3-(1-methyl-2-piperidylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpiperidine (7.43 g.; 0.05 mole) is converted to free base by adding 5 mls. of 50% NaOH 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 stirred at room temperature and 5.96 g. (0.05 mole) of phenylisocyanate, dissolved in anhydrous benzene, is added dropwise. Cloudiness occurs and eventually solid precipitates from the solution. The reaction mixture is stirred at room temperature overnight (about 17 hours). The solid is collected, m.p. = 145°-158° C. The filtrate is taken to dryness in vacuo to give further solid material. Repeated recrystallizations of the combined solids from methanol yields the pure product, 1-phenyl-3-(1-methyl-2-piperidylidene)urea, m.p. = 160°-161° C.

Workup

  1. additionby adding 5 mls
  2. extractionextracting with benzene
  3. dry with materialAfter drying over K2CO3 the benzene solution
  4. additionis added dropwise
  5. customeventually solid precipitates from the solution
  6. stirringThe reaction mixture is stirred at room temperature overnight (about 17 hours)
  7. customThe solid is collected
  8. customto give further solid material
  9. customrecrystallizations of the combined solids from methanol

Sources & evidence

ORD record
ord-cb6eaf8bfd844883b80a25dc343eb40d
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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