p-Toluenesulfonic acid → 2-Bromo-4-(4-methylpiperazin-1-yl)phenyl acetate

HRID 45808Notes

Reaction equation

HRID 45808 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:29]Br>C(#N)C.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]2)=[CH:9][C:10]=1[Br:29])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 24408BromineHCID 679737964-(4-Methylpiperazin-1-yl)phenyl acetate

Product 1

HCID 679736642-Bromo-4-(4-methylpiperazin-1-yl)phenyl acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-methylpiperazin-1-yl)phenyl acetate 247 mg (1.05 mmol) and p-toluenesulfonic acid 209 mg (1.1 mmol) in acetonitrile was cooled in an ice bath and bromine 0.056 ml (1.1 mmol) was added dropwise. The reaction was stirred at room temperature until complete (3-4 hours), was diluted with ethyl acetate and extracted with water and saturated NaHCO3. The organic phase, dried over Na2SO4 and evaporated, was purified by flash chromatography (DCM/MeOH 85/15) to give the product as a dark brown oil. HPLC (254 nm) method 2 Rt 4.05 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H) 2.36 (s, 3H) 2.39 (m, 4H) 3.44 (m, 4H) 6.50 (dd. J=2.1, 8.3 Hz, 1H) 7.03 (d, J=8.3 Hz, 1H) 7.21 (d, J=2.1 Hz, 1H). Mass. Calc. 313.0546 Mass. Found: 313.0538

Workup

  1. extractionextracted with water and saturated NaHCO3
  2. dry with materialThe organic phase, dried over Na2SO4
  3. customevaporated
  4. customwas purified by flash chromatography (DCM/MeOH 85/15)

Sources & evidence

ORD record
ord-c784f788c35a4ab4831870a108a1a15f
Source dataset
uspto-grants-2013_09
Patent number
US08541576B2

Reaction notes

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