Triethylamine → 1-[[2-(4-Methoxyphenyloxy)ethyl]carbamoyl]-2-oxopyrrolidine

HRID 892725Notes

Reaction equation

HRID 892725 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][NH2:28])=[CH:21][CH:20]=1.C(N(CC)CC)C>>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][C:7]([N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])=[O:8])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 144410901-Phenoxycarbonyl-2-oxopyrrolidineHCID 197698612-(4-Methoxyphenyloxy)ethylamine hydrobromide

Product 1

HCID 144411461-[[2-(4-Methoxyphenyloxy)ethyl]carbamoyl]-2-oxopyrrolidineYield 118.5%

Conditions

Temperature
110 °C

Procedure

A mixture of 1.16 g (5.64 mmol) of 2-oxo-1-phenoxycarbonylpyrrolidine (II) were added 2.0 g (8.06 mmol) of 2-(4-methoxyphenyloxy)-ethylamine hydrobromide and 1.63 g (16.1 mmol) of triethylamine was heated at 110° C. for 3 hr. After evaporation of the solvent, the residue was refined by silica gel column chromatography, whereby 1.86 g of the objective compound (Ia-42) was obtained as crystals from the eluate with toluene/ethyl acetate (5/1-3/1 v/v). Yield: 83.0%.

Workup

  1. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-7e19def7ab0b4bf6a0eb04ac7733bf90
Source dataset
uspto-grants-1992_06
Patent number
US05120733

Reaction notes

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