4-Fluorophenol → HCID 11544175, compound

HRID 1367698Notes

Reaction equation

HRID 1367698 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])[CH2:4][CH2:3]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](O)=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 2232842-(4-Methyl-piperazin-1-yl)-1-phenyl-ethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 11544175HCID 11544175, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Methyl-piperazin-1-yl)-1-phenyl-ethanol (38) (2.0 g, 9.09 mmol) was dissolved in 50 mL of THF. 4-fluorophenol was added to the solution and then triphenylphosphine. After complete dissolution, the mixture was cooled to 0° C. and after 10 minutes DIAD was added dropwise. Ice-bath was removed and the reaction mixture was stirred at room temperature for 48 hours. The product was purified using flash chromatography, eluting pure ethyl acetate to recover any starting materials. Polarity of the solvent was then increased using 30:70 methanol/ethyl acetate. The product 13a (2.18 g, 6.94 mmol, 76%) was afforded as a orange-brown oil. 1H-NMR (CDCl3): δ 7.33 (5H, m), 6.80 (4H, m), 5.21 (1H, dd, J=3.08, 3.07 Hz), 3.00 (1H, dd, J=8.49, 8.48), 2.67 (5H, b), 2.45 (4H, b), 2.27 (3H, s).

Workup

  1. dissolutionAfter complete dissolution
  2. additionwas added dropwise
  3. customIce-bath was removed
  4. customThe product was purified
  5. washeluting pure ethyl acetate
  6. customto recover any starting materials
  7. temperaturePolarity of the solvent was then increased

Sources & evidence

ORD record
ord-856af19ffc0940b3bf9068f08afba6f3
Source dataset
uspto-grants-2011_02
Patent number
US07893261B2

Reaction notes

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