Carbamic chloride, N-methyl-N-phenyl- → 1-Methyl-3-(1-methyl-2-piperidylidene)-1-phenylurea

HRID 2071527Notes

Reaction equation

HRID 2071527 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[CH3:9][N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11](Cl)=[O:12]>C1C=CC=CC=1>[CH3:9][N:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([N:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8])=[O:12]

Participants

4

Reactant 2

HCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 124490281-Methylpiperidin-2-imine

Product 1

HCID 541590611-Methyl-3-(1-methyl-2-piperidylidene)-1-phenylurea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpiperidine (14.8 g.; 0.1 mole) is converted to free base by adding 10 ml. of 50% NaOH and extracting into benzene. After drying over K2CO3, the benzene layer is stirred at room temperature and 8.84 g. (0.05 mole) of N-methyl-phenylcarbamoyl chloride (prepared according to the method of J. A. Aeschlimann, U.S. Pat. No. 2,449,440), dissolved in anhydrous benzene, is added dropwise to this solution. The mixture is stirred at room temperature overnight (about 17 hours) and then filtered. The filtrate is taken to dryness in vacuo and the residue is dissolved in and recrystallized from hexane to give the product, 1-methyl-3-(1-methyl-2-piperidylidene)-1-phenylurea.

Workup

  1. additionby adding 10 ml
  2. extractionof 50% NaOH and extracting into benzene
  3. dry with materialAfter drying over K2CO3
  4. additionis added dropwise to this solution
  5. stirringThe mixture is stirred at room temperature overnight (about 17 hours)
  6. filtrationfiltered
  7. dissolutionthe residue is dissolved in and
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-d7a626211487483da401d91764084f7b
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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