Toluene → 1255204-84-2

HRID 1187100Notes

Reaction equation

HRID 1187100 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:7][C:8]1[C:16]2[CH2:15][O:14][C:13](=[O:17])[C:12]=2[CH:11]=[CH:10][C:9]=1[C@@H:18]1[CH2:20][O:19]1.[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C)[C:30](=[O:32])[CH3:31]>>[N:1]1([CH2:31][C@@H:30]([C:22]2[CH:23]=[CH:24][C:25]3[C:13](=[O:17])[O:14][CH2:15][C:26]=3[C:21]=2[CH3:27])[OH:32])[CH2:6][CH2:5][N:4]([CH2:20][C@@H:18]([C:9]2[CH:10]=[CH:11][C:12]3[C:13](=[O:17])[O:14][CH2:15][C:16]=3[C:8]=2[CH3:7])[OH:19])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 4837PiperazineHCID 31374DimethylacetamideHCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

Product 1

HCID 595687131255204-84-2

Conditions

Temperature
110 °C

Procedure

Piperazine (4.51 g, 52.4 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (20.0 g, 105 mmol) were charged to a 3-neck 500-mL roundbottom flask, equipped with a reflux condenser, under nitrogen. Toluene (80.0 mL, 751 mmol) and N,N-dimethylacetamide (80 mL, 854 mmol) were added to provide a suspension. The reaction mixture was warmed to 110° C., becoming homogeneous at 25° C. After stirring for 4.5 h at 110° C., the temperature was increased to 115° C. to drive the reaction forward. After stirring for 48 h, the reaction mixture was cooled to RT. On cooling, crystallization occurred. Water was added via addition funnel (45 mL), generating a thick slurry. The suspension was filtered and the solids were washed with 4:1 water:DMA (60 mL), followed by water (2×35 mL). The solid was dried on the funnel under vacuum with a nitrogen sweep to constant mass. 5,5′-{Piperazine-1,4-diylbis[(1R)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one) was isolated. 1H-NMR (500 MHz, CDCl3) δ ppm 7.80 (s, 4H), 5.25 (s, 4H), 5.11 (d, J=11 Hz, 2H), 4.30-3.51 (broad, 2H), 2.90 (broad, 4H), 2.69-2.50 (m, 6H), 2.44 (t, J=11 Hz, 2H), 2.30 (s, 6H).

Workup

  1. customequipped with a reflux condenser, under nitrogen
  2. customto provide a suspension
  3. custombecoming homogeneous at 25° C
  4. temperaturethe temperature was increased to 115° C.
  5. customthe reaction forward
  6. stirringAfter stirring for 48 h
  7. temperaturethe reaction mixture was cooled to RT
  8. temperatureOn cooling
  9. customcrystallization
  10. additionWater was added via addition funnel (45 mL)
  11. filtrationThe suspension was filtered
  12. washthe solids were washed with 4:1 water
  13. customThe solid was dried on the funnel under vacuum with a nitrogen sweep to constant mass

Sources & evidence

ORD record
ord-ef2870c6ef02482999038640946441d2
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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