1,3-Bis(2,3-epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)propane → HCID 67208027, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence