Ethanol → 5-[2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-(methyloxy)ethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 1187108Notes

Reaction equation

HRID 1187108 reaction equation
Cl.[CH3:2][C:3]1[C:11]2[CH2:10][O:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:13]([O:21][CH3:22])[CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[CH3:23][C:24]1[C:32]2[CH2:31][O:30][C:29](=[O:33])[C:28]=2[CH:27]=[CH:26][C:25]=1[CH:34]1[CH2:36][O:35]1.CCO>C1COCC1>[OH:35][CH:34]([C:25]1[CH:26]=[CH:27][C:28]2[C:29](=[O:33])[O:30][CH2:31][C:32]=2[C:24]=1[CH3:23])[CH2:36][N:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH:13]([C:4]2[CH:5]=[CH:6][C:7]3[C:8](=[O:12])[O:9][CH2:10][C:11]=3[C:3]=2[CH3:2])[O:21][CH3:22])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 684302344-methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride

Product 1

HCID 498044835-[2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-(methyloxy)ethyl]-4-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

4-Methyl-5-[1-(methyloxy)-2-piperazin-1-ylethyl]-2-benzofuran-1(3H)-one hydrochloride (40 mg, 0.14 mmol), 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (79 mg, 0.41 mmol), were added to a 5 mL microwave tube containing a stir bar; to the mixture was added EtOH (2 mL) and THF (0.5 Ml). The tube was capped, degassed and purged with N2. It was then placed in a microwave reactor and heated at 120° C. for 1 hour; LC indicated completion of the reaction. The solution was concentrated to dryness, dissolved in MeOH (3.5 Ml), filtered and was then purified by mass-directed HPLC to give 5-[2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-1-(methyloxy)ethyl]-4-methyl-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 481 [M+1]+.

Workup

  1. additioncontaining a stir bar
  2. customThe tube was capped
  3. customdegassed
  4. custompurged with N2
  5. customIt was then placed in a microwave reactor
  6. customcompletion of the reaction
  7. concentrationThe solution was concentrated to dryness
  8. dissolutiondissolved in MeOH (3.5 Ml)
  9. filtrationfiltered
  10. customwas then purified by mass-directed HPLC

Sources & evidence

ORD record
ord-5fd10a626cfa4bcf86ce95322299a8a7
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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