4-Hydroxybenzoic Acid → HCID 28798584, compound

HRID 1674988Notes

Reaction equation

HRID 1674988 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[CH2:15][CH2:14][N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:12][CH2:11]2)[CH3:9])=[CH:4][CH:3]=1.OC1C=CC(C(O)=O)=CC=1.O>Br>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 962WaterHCID 67340847HCID 67340847, compound

Product 1

HCID 28798584HCID 28798584, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
5 °C

Procedure

(R)-1-(1-(4-Bromophenyl)ethyl)-4-tosylpiperazine (4.44 g, 10.49 mmol) and 4-hydroxybenzoic acid (4.35 g, 31.46 mmol) in hydrobromic acid (33% in AcOH, 40 mL,) were stirred at room temperature for 48 hours. Water (40 mL) was then added to the dark mixture and stirring continued for a further 2 hours to give a beige solid, which was filtered off and washed with water (10 mL). The combined filtrate and washings were washed with toluene (3×50 mL) then cooled to 5° C. and basified to pH>10 with 40% NaOH. The resulting mixture was extracted with tert butyl methyl ether (2×50 mL) and the combined extracts washed with saturated brine, dried over MgSO4 and evaporated to give (R)-1-[1-(4-bromophenyl)ethyl]piperazine (2.69 g, 95%) as an orange, viscous oil.

Workup

  1. customto give a beige solid, which
  2. filtrationwas filtered off
  3. washwashed with water (10 mL)
  4. washThe combined filtrate and washings were washed with toluene (3×50 mL)
  5. extractionThe resulting mixture was extracted with tert butyl methyl ether (2×50 mL)
  6. washthe combined extracts washed with saturated brine
  7. dry with materialdried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-55de1ef5ce1946b18237d68991d13e76
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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