2-(Trifluoromethyl)oxirane → HCID 70927031, compound

HRID 467517Notes

Reaction equation

HRID 467517 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.[N:8]1([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>CN1CCCC1>[F:1][C:2]([F:7])([F:6])[CH:3]([OH:5])[CH2:4][N:11]1[CH2:10][CH2:9][N:8]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 5207692-(Trifluoromethyl)oxirane2×HCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 70927031HCID 70927031, compound

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
80 °C

Procedure

0.47 ml of 1,1,1-trifluoro-2,3-epoxypropane is added to a solution of 1 g of benzyl piperazine-1-carboxylate in 100 ml of N-methylpyrrolidine and it is heated at 80° C. for 12 hours. 0.05 ml of 1,1,1-trifluoro-2,3-epoxypropane is added and it is heated at 80° C. for 48 hours, The reaction mixture is extracted with DCM, the organic phase is washed with a 4% solution of LiCl in water, it is dried over MgSO4 and the solvent is evaporated under vacuum. The residue is purified by preparative HPLC and 1.7 g of the expected compound is obtained.

Workup

  1. temperatureit is heated at 80° C. for 48 hours
  2. extractionThe reaction mixture is extracted with DCM
  3. washthe organic phase is washed with a 4% solution of LiCl in water, it
  4. dry with materialis dried over MgSO4
  5. customthe solvent is evaporated under vacuum
  6. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-323a858f3efb462983d60faec65fa366
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

Loading…