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

HRID 37863Notes

Reaction equation

HRID 37863 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-pyridin-2-yl)-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 overnight 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 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 successively with water (2×30 mL) then brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue. Trituration with petroleum ether afforded 2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenol (510 mg, 90%) as a brownish-yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  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 successively with water (2×30 mL)
  9. dry with materialbrine (30 mL), dried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto give a residue

Sources & evidence

ORD record
ord-b63af61107634fb5b50ec1600112f82a
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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