Piperazine → HCID 86719479, compound

HRID 1772231Notes

Reaction equation

HRID 1772231 reaction equation
I[CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:5]=2[O:4]1.C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC#N>[F:13][C:12]([F:15])([F:14])[C:9]1[CH:10]=[CH:11][C:5]2[O:4][CH:3]([CH2:2][N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH2:7][C:6]=2[CH:8]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 86719480HCID 86719480, compound

Product 1

HCID 86719479HCID 86719479, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(iodomethyl)-5-(trifluoromethyl)-2,3-dihydro-1-benzofuran (2.8 g, 8.5 mmol) in CH3CN (40 ml) was added potassium carbonate (2.36 g, 17.1 mmol, 2 eq) and piperazine (2.94 g, 34.1 mmol, 4 eq) at room temperature. The mixture was heated at reflux for 3 hours, the solids were filtered off, and the filtrate was concentrated under vacuum. The crude material was purified by silica gel chromatography using 1-2.5% methanol in dichloromethane to elute. The product-containing fractions were combined and concentrated under vacuum to afford 1-[[5-(trifluoromethyl)-2,3-dihydro-1-benzofuran-2-yl]methyl]piperazine as light yellow oil (1.25 g, 51%); (ES, m/z): [M+H]+ 287; 1H NMR (300 MHz, CDCl3): δ 7.37 (d, J=9.0 Hz, 2H), 6.83 (d, J=8.4 Hz, 1H), 5.00-5.10 (m, 1H), 3.26-3.35 (m, 1H), 2.96-3.04 (m, 1H), 2.88-2.95 (m, 4H), 2.78-2.80 (m, 1H), 2.54-2.69 (m, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationthe solids were filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude material was purified by silica gel chromatography
  6. washto elute
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-26a7ca233394403aa6abc18918ab0fa0
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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