2,2'-[(2,2-Bis{[(oxiran-2-yl)methoxy]methyl}propane-1,3-diyl)bis(oxymethylene)]bis(oxirane) → HCID 67208027, compound

Temperature

60 °C

To a 10 mL round bottom flask containing a stir bar was added methyl isobutyliminoethylpiperazine (726 mg, 3.44×10−3 moles, 3 equivalents) and 4 g MeOH. To this mixture at 25° C. was added pentaerythritol tetraglycidyl ether (307 mg, 0.853 mmol, 3.4 mmoles epoxide). This mixture was stirred and heated at 60° C. for 6.5 hours. To this mixture was added ethyl t-piperazine carbamate (537 mg, 3.4 mmol) and this mixture heated at 60° C., 16 hours, 60° C., 54 h with no adduct for the desired product at 906 or 833 (decarboxylated material). Another aliquot of monoblocked piperazine was added (1.5 g) and this mixture was heated at 70° C., 16 hours, 24 hours and 60 hours total with no sign of desired adduct. The 3:1 adduct at 748 amu was completely converted to 4:1 adduct at 993 amu by reaction of remaining equivalent imine in presence of a total of 16 equivalents of ethyl 1-piperazine carboxylate. This mixture was purified by tangential flow ultrafiltration using a 1K regenerated cellulose membrane at 20 psi as a 2-5% w/w mixture in MeOH to give 8-9 recirculations. The retentate was stripped of volatiles on a rotary evaporator followed by high vacuum to give 590 mg. The following scheme illustrates this reaction.

1. additionTo a 10 mL round bottom flask containing a stir bar

ORD record

ord-b6ac0fe055b14486bfe1e3dcad7159a8

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977452B2