Benzylamine → 1-(2-Benzylaminoacetyl)-2,2-dimethyl-4-imidazolidinone

HRID 256357Notes

Reaction equation

HRID 256357 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:9][C:8](=[O:10])[NH:7][C:6]1([CH3:12])[CH3:11])=[O:4].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][CH2:2][C:3]([N:5]1[CH2:9][C:8](=[O:10])[NH:7][C:6]1([CH3:12])[CH3:11])=[O:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 201637141-(2-Bromoacetyl)-2,2-dimethyl-4-imidazolidinone

Product 1

HCID 201637261-(2-Benzylaminoacetyl)-2,2-dimethyl-4-imidazolidinone

Procedure

A solution of 1-(2-bromoacetyl)-2,2-dimethyl-4-imidazolidinone (1.9 g) in 8.8 ml of benzylamine was stirred at room temperature for 4 hours. The excess of benzylamine was removed under reduced pressure (about 5 mmHg) at 80° C. The residue was taken up with ethyl acetate and the precipitate filtered off. The filtrate was evaporated and the residue was chromatographed on a silica gel column by eluting with dichloromethane/methanol 7:3. The selected fractions were collected and evaporated. Trituration of the residue with ether gave 1 g of the title compound as a white powder, m.p. 131°-132° C.

Workup

  1. customThe excess of benzylamine was removed under reduced pressure (about 5 mmHg) at 80° C
  2. filtrationthe precipitate filtered off
  3. customThe filtrate was evaporated
  4. customthe residue was chromatographed on a silica gel column
  5. washby eluting with dichloromethane/methanol 7:3
  6. customThe selected fractions were collected
  7. customevaporated

Sources & evidence

ORD record
ord-5b4db8fd8c1a4af993346b5d39825ee2
Source dataset
uspto-grants-1987_10
Patent number
US04703054

Reaction notes

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