4-Chlorophenyl Isocyanate → Urea, N-(4-chlorophenyl)-N'-((5-oxo-1-(phenylmethyl)-3-pyrrolidinyl)methyl)-

HRID 34521Notes

Reaction equation

HRID 34521 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](=[O:15])[CH2:4]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>O1CCOCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:1][CH2:2][CH:3]2[CH2:7][N:6]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5](=[O:15])[CH2:4]2)=[O:25])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 65926Nebracetam

Product 1

HCID 3025488Urea, N-(4-chlorophenyl)-N'-((5-oxo-1-(phenylmethyl)-3-pyrrolidinyl)methyl)-Yield 74.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

52 g (0.25 mol) of 4-aminomethyl-1-benzylpyrrolidin-2-one are stirred for 2 hours at ambient temperature in 70 ml of dioxane with 38 g (0.25 mol) of p-chlorophenylisocyanate and the solution is then evaporated in vacuo. The residue crystallizes out of ethyl acetate to yield 67 g of the title compound, m.p. 139°-140° C.

Workup

  1. customthe solution is then evaporated in vacuo
  2. customThe residue crystallizes out of ethyl acetate

Sources & evidence

ORD record
ord-d3153c2d0dfa4fb0acb77b87e480d96d
Source dataset
uspto-grants-1988_08
Patent number
US04762832

Reaction notes

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