Triethylamine → 2-(2-Phenylpropyl)imidazolidin-4-one

HRID 1948390Notes

Reaction equation

HRID 1948390 reaction equation
[C:1]1([CH:7]([CH3:11])[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:13][CH2:14][C:15]([NH2:17])=[O:16].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:1]1([CH:7]([CH3:11])[CH2:8][CH:9]2[NH:17][C:15](=[O:16])[CH2:14][NH:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 859793-PhenylbutanalHCID 2723639Glycinamide hydrochloride

Product 1

HCID 575228982-(2-Phenylpropyl)imidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-phenylbutanal (Trifernal®, 0.67 g, 4.5 mmol), glycinamide hydrochloride (0.50 g, 4.5 mmol), triethylamine (0.46 g, 4.5 mmol) and K2CO3 in ethanol (4 ml) was heated to 60° C. for 24 h. Then the solvent was removed under vacuum at 40° C. The residue was taken up in ether and the solvent evaporated to yield 0.52 g (57%) of a highly viscous oil as a mixture of diastereoisomers.

Workup

  1. customThen the solvent was removed under vacuum at 40° C
  2. customthe solvent evaporated
  3. customto yield 0.52 g (57%) of a highly viscous oil
  4. additionas a mixture of diastereoisomers

Sources & evidence

ORD record
ord-625699e9e27741c5be5c208f1d623f40
Source dataset
uspto-grants-2013_03
Patent number
US08399499B2

Reaction notes

Loading…