1-Methylpiperazine → HCID 22757253, compound

HRID 58974Notes

Reaction equation

HRID 58974 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:18](OC)=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13](OC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCNCC1>C1(C)C=CC=CC=1.C1COCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:18]=[O:19])[CH:11]=[C:12]([CH:17]=1)[CH:13]=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 1046681,3-Benzenedicarboxylic acid, 5-phenoxy-, dimethyl ester

Product 1

HCID 22757253HCID 22757253, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-phenoxyisophthalate (0.143 g, 0.50 mmol) in toluene (12 mL) was added drop-wise a solution of Red-A1 (60% in toluene, 0.673 mL, 2.0 mmol) and 1-methylpiperazine (0.243 mL, 2.2 mmol) in THF at 5° C., and the resulting mixture was stirred for 2 h. The reaction was quenched with H2O (4 mL), and then extracted with EtOAc (20 mL). The organic layer was washed with H2O (10 mL), dried over anhydrous Na2SO4, and then concentrated under reduced pressure. Purification by flash column chromatography (10% EtOAc/hexanes) afforded the desired product (0.094 g, 83%) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 10.04 (s, 2H), 8.08 (s, 1H), 7.72 (t, J=1.5 Hz, 2H), 7.46-7.40 (m, 2H), 7.28-7.24 (m, 1H), 7.09-7.06 (m, 2H).

Workup

  1. customThe reaction was quenched with H2O (4 mL)
  2. extractionextracted with EtOAc (20 mL)
  3. washThe organic layer was washed with H2O (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d875d10a633544aa973ae7b553b75d87
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

Loading…