4-(Benzyloxy)phenyl isocyanate → 1-(4-Benzyloxyphenyl)-3-(1-methyl-2-piperidylidene)urea

HRID 1973954Notes

Reaction equation

HRID 1973954 reaction equation
[NH:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH3:8].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1C=CC=CC=1>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:1]=[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][N:3]2[CH3:8])=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 2562684-(Benzyloxy)phenyl isocyanateHCID 124490281-Methylpiperidin-2-imine

Product 1

HCID 539156231-(4-Benzyloxyphenyl)-3-(1-methyl-2-piperidylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The hydrochloride salt of 2-imino-1-methylpiperidine (7.43 g.; 0.05 mole) is converted to the free base in benzene in the usual manner. After drying over K 2 CO 3 and filtering, a benzene solution of 0.05 mole of p-benzyloxyphenylisocyanate is added dropwise with stirring. After addition is complete, further stirring is continued for about 6 hours at room temperature. The benzene is evaporated in vacuo and the solid residue is recrystallized from methanol to give the product 1-(4-benzyloxyphenyl)-3 -(1-methyl-2-piperidylidene)urea.

Workup

  1. dry with materialAfter drying over K 2 CO 3
  2. filtrationfiltering
  3. additionAfter addition
  4. stirringfurther stirring
  5. customThe benzene is evaporated in vacuo
  6. customthe solid residue is recrystallized from methanol

Sources & evidence

ORD record
ord-1196447e2ba346a48bb709e7db53e587
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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