1-Piperazinecarboxylic acid, ethyl ester → 4-(1,4-Dihydro-3-methyl-1, 4-dioxo-2-naphthalenyl)-1-piperazinecarboxylic acid, ethyl ester

HRID 622393

Reaction equation

O1[C:11]2([CH3:12])[CH:2]1[C:3](=[O:14])[C:4]1[C:9]([C:10]2=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:15]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C(O)C>[CH3:12][C:11]1[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:14])[C:2]=1[N:18]1[CH2:17][CH2:16][N:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1.88 g of 2,3-epoxy-3-methyl-1,4-naphthoquinone, 3.16 g of piperazinecarboxylic acid, ethyl ester and 100 ml of absolute ethanol was stirred for 12 hours at 50°C. The solvent was then removed and the remainder filtered through a one inch plug of silica gel and eluted with chloroform. The eluate was evpaorated, giving 1 g of the desired product as a viscous red oil.

Workup

customThe solvent was then removed
filtrationthe remainder filtered through a one inch plug of silica gel
washeluted with chloroform

Sources & evidence

ORD record: ord-46c1213e5f3d46c9a61253a3964493a3
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04771061

Linked notes

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