Acetyl chloride → 1-(4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethan-1-one

HRID 57565Notes

Reaction equation

HRID 57565 reaction equation
Cl.[CH3:2][C:3]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][B:5]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:29](Cl)(=[O:31])[CH3:30]>C1COCC1>[CH3:9][C:7]1([CH3:8])[C:3]([CH3:22])([CH3:2])[O:4][B:5]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:29](=[O:31])[CH3:30])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[O:6]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10796Cesium carbonateHCID 710936951-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine hydrochloride

Product 1

HCID 532171411-(4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl) piperazine hydrochloride (419 mg, 1.29 mmol) and cesiumcarbonate (1.27 g, 3.9 mmol) in THF (30 mL) was added acetyl chloride (0.5 mL, 6.5 mmol). Then the mixture was stirred at room temperature overnight, extracted with EA, washed with NaHCO3 solution and brine. The organic solution was concentrated and purified by flash column chromatography, eluting with PE/EA, to give product as a white solid. MS (m/z): 331 (M+H)+.

Workup

  1. extractionextracted with EA
  2. washwashed with NaHCO3 solution and brine
  3. concentrationThe organic solution was concentrated
  4. custompurified by flash column chromatography
  5. washeluting with PE/EA
  6. customto give product as a white solid

Sources & evidence

ORD record
ord-f7f3a78685bb4c21806c8f77659c5485
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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