Hydrochloric Acid → 2-[4-(4,6-Dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenol

HRID 880476Notes

Reaction equation

HRID 880476 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[N:32]=2)[CH2:27][CH2:26]1)C1C=CC=CC=1.Cl>>[CH3:37][C:35]1[CH:34]=[C:33]([CH3:38])[N:32]=[C:31]([N:28]2[CH2:27][CH2:26][N:25]([C:17]3[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=3[OH:15])[CH2:30][CH2:29]2)[CH:36]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 66851896HCID 66851896, compound

Product 1

HCID 668512292-[4-(4,6-Dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenolYield 90.3%

Procedure

Trifluoroacetic acid (5 mL) was added to 1-(2-benzyloxy-4-nitro-phenyl)-4-(4,6-dimethyl-2-pyridyl)piperazine (720 mg, 1.72 mmol) at between 0 and 5° C. followed by concentrated hydrochloric acid (2 mL). The mixture was heated at reflux for 16 h then cooled to between 0 and 5° C. and quenched with saturated sodium bicarbonate solution (30 mL). Chloroform (30 mL) was added and the mixture was stirred for 15 min. The organic phase was separated and the aqueous phase was extracted with chloroform (30 mL). The combined organic phases were washed with water (2×30 mL), brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a crude residue. Trituration with petroleum ether afforded 2-[4-(4,6-dimethyl-2-pyridyl)piperazin-1-yl]-5-nitro-phenol (510 mg, 90%) as a brownish-yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturethen cooled to between 0 and 5° C.
  4. customquenched with saturated sodium bicarbonate solution (30 mL)
  5. additionChloroform (30 mL) was added
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with chloroform (30 mL)
  8. washThe combined organic phases were washed with water (2×30 mL), brine (30 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a crude residue

Sources & evidence

ORD record
ord-2e770a4230a14e15886cb84a849140f9
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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