Trifluoroacetic acid → HCID 22122160, compound

Reaction equation

[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9](CC2C=CC(OC)=CC=2OC)[C:8](=[O:23])[C:7]1=[O:24])=[N+:2]=[N-:3].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[N:1]([CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:23])[C:7]1=[O:24])=[N+:2]=[N-:3]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 22122227HCID 22122227, compound

Product 1

HCID 22122160HCID 22122160, compoundYield 89.7%

Procedure

A mixture of 3.65 g of 1-(2-azidoethyl)-4-(2,4-dimethoxybenzyl)-2,3-dioxopiperazine, 14.6 ml of trifluoroacetic acid and 7.3 ml of anisole was refluxed for 2 hours. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 1.8 g of 1-(2-azidoethyl)-2,3-dioxopiperazine as an oil.

Workup

temperaturewas refluxed for 2 hours
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-de2715a7631f4703a24381749a8306dc
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153613

Reaction notes

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