Water → HCID 8690650, compound

HRID 2353251Notes

Reaction equation

HRID 2353251 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:15]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 92467p-(1-Piperazinyl)phenolHCID 516892Sodium Bicarbonate

Product 1

HCID 8690650HCID 8690650, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-piperazin-1-yl-phenol (1.78 g, 10 mmol) in DMF (20 mL) was added bromomethyl-benzene (1.71 g, 10 mmol) dropwise and then the reaction was stirred at room temperature for 16 h. The mixture was poured into water and pH was adjusted to 7 with sat. aqueous NaHCO3, and then extracted with ethyl acetate (100 ml×2). The combined organic layers were washed with water and dried over anhy. Na2SO4. After removing the solvent under vacuum, the title compound was obtained (1.1 g, 41%) and MS (ESI) m/z 269 (M+H). 1H NMR (400 MHz, CDCl3) δ 2.62 (t, J=4.8 Hz, 4H), 3.08 (t, J=4.8 Hz, 4H), 3.57 (s, 2H), 6.74 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 7.28-7.34 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe combined organic layers were washed with water
  3. customdried over anhy
  4. customAfter removing the solvent under vacuum

Sources & evidence

ORD record
ord-30eb2155e44345f0aba4b8fb2a35bc92
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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