Triethylamine → 1-[N-Methyl[2-(4-methoxyphenyloxy)ethyl]carbamoyl]-2-oxopyrrolidine

HRID 1110781Notes

Reaction equation

HRID 1110781 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7](OC1C=CC=CC=1)=[O:8].Br.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][CH3:29])=[CH:21][CH:20]=1.C(N(CC)CC)C.C(OCC)(=O)C>CC(N(C)C)=O>[CH3:29][N:28]([CH2:27][CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)[C:7]([N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 144410901-Phenoxycarbonyl-2-oxopyrrolidineHCID 197698602-(4-methoxyphenyloxy)ethyl-N-methylamine hydrobromide

Product 1

HCID 144411451-[N-Methyl[2-(4-methoxyphenyloxy)ethyl]carbamoyl]-2-oxopyrrolidineYield 88.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 1.87 g (9.13 mmol) of 2-oxo-1-phenoxycarbonylpyrrolidine (II), 2.39 g (9.13 mmol) of 2-(4-methoxyphenyloxy)ethyl-N-methylamine hydrobromide and 2.30 g (22.8 mmol) of triethylamine in 0.5 ml of DMA was heated at 115°-125° C. for 6.5 hr. and ethyl acetate was added to the reaction solution. The mixture was washed with aqueous NaHCO3 and water, and dried, then the solvent was distilled off. The residue was refined by silica gel column chromatography, whereby 2.37 g of an oily compound (I a-41) was obtained from the eluate with toluene/ethyl acetate (5/1-3/1 v/v). Yield: 88.8%

Workup

  1. temperaturewas heated at 115°-125° C. for 6.5 hr
  2. washThe mixture was washed with aqueous NaHCO3 and water
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4bb2365c0ea741c48305399dc3df404f
Source dataset
uspto-grants-1990_12
Patent number
US04977167

Reaction notes

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