Water → (S)-2-(4-benzyl-1-(2-bromo-5-methylphenyl)piperazin-2-yl)ethanol

HRID 1896135Notes

Reaction equation

HRID 1896135 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1F.CC(C)([O-])C.[Na+].O>CS(C)=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=2[Br:17])[C@@H:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5732804-Bromo-3-fluorotolueneHCID 23395653(S)-2-(4-benzylpiperazin-2-yl)ethanolHCID 23676156Sodium t-butoxide

Product 1

HCID 66769566(S)-2-(4-benzyl-1-(2-bromo-5-methylphenyl)piperazin-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(4-benzylpiperazin-2-yl)ethanol (150 mg, 0.681 mmol) and 1-bromo-2-fluoro-4-methylbenzene (167 mg, 885 mmol) in dimethyl sulfoxide (5 mL) was added sodium tert-butoxide (164 mg, 1.70 mmol). The reaction mixture was allowed to stir for 16 hours at room temperature before addition of water and ethyl acetate. The organic layer was separated and concentrated onto silica gel. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.40 (d, J=7.80 Hz, 1 H), 7.18-7.35 (m, 5 H), 6.92 (d, J=1.36 Hz, 1 H), 6.65-6.73 (m, 1 H), 4.08 (t, J=6.44 Hz, 2 H), 3.36-3.51 (m, 2 H), 2.55-2.89 (m, 6 H), 1.87-1.99 (m, 1 H), 1.68-1.77 (m, 2 H); MS (APCI+) m/z 389, 391 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated onto silica gel
  3. customPurification via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a30edc3092ff42278eeac614ac1aadbf
Source dataset
uspto-grants-2013_08
Patent number
US08518933B2

Reaction notes

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