N~1~-(4-Methoxyphenyl)ethane-1,2-diamine → 1-[[2-(4-Methoxyphenyl)aminoethyl]carbamoyl]-2-oxopyrrolidine

HRID 1590192Notes

Reaction equation

HRID 1590192 reaction equation
O([C:8]([N:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])=[O:9])C1C=CC=CC=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH2:25][CH2:26][NH2:27])=[CH:20][CH:19]=1>C(OC(=O)C)C.C1(C)C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH2:25][CH2:26][NH:27][C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[O:9])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 12666396N~1~-(4-Methoxyphenyl)ethane-1,2-diamineHCID 144410901-Phenoxycarbonyl-2-oxopyrrolidine

Product 1

HCID 144410931-[[2-(4-Methoxyphenyl)aminoethyl]carbamoyl]-2-oxopyrrolidineYield 91.4%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 4.0 g (19.5 mmol) of 1-phenoxycarbonyl-2-oxopyrrolidine and 3.4 g (20.4 mmol) of 2-(4-methoxyphenylamino)ethylamine was heated at 115°-120° C. for 4 hr. The reaction solution was refined by silica gel column chromatography, whereby 4.94 g (87.0%) of the objective product (Ia-1) was obtained from the eluate with toluene - ethyl acetate (3/1 v/v). The needles melting at 83.5°-84.5° C. were obtained by recrystallizing from ethanol.

Workup

  1. temperaturewas heated at 115°-120° C. for 4 hr

Sources & evidence

ORD record
ord-86cb32a0a41c4a5492e73483e4338400
Source dataset
uspto-grants-1993_04
Patent number
US05202345

Reaction notes

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