Hydrochloric Acid → HCID 67106694, compound

HRID 1910813Notes

Reaction equation

HRID 1910813 reaction equation
Cl.C([O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)[CH:14]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([N:22]2[CH2:21][CH2:20][N:19]([C:15]3[CH:14]=[C:13]([O:12][CH2:11][CH2:10][OH:9])[CH:18]=[CH:17][N:16]=3)[CH2:24][CH2:23]2)=[CH:26][CH:27]=1)([O-:33])=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67106465HCID 67106465, compound

Product 1

HCID 67106694HCID 67106694, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
72.5 °C

Procedure

Conc. HCl (6 mL, 65.7 mmol) was added to a solution of 1-[4-(2-benzyloxy-ethoxy)-pyridin-2-yl]-4-(4-nitrophenyl)-piperazine-(0.8 g, 1.84 mmol) in TFA (10 mL) at r.t. followed by heating to 70-75° C. for 7 h. The excess TFA and HCl were evaporated, the residue diluted with water and basified with saturated aq. sodium bicarbonate solution to pH 8-9 and extracted with dichloromethane. The organic layer was washed with water followed by brine solution and dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was triturated with petroleum ether to afford 2-{2-[4-(4-nitrophenyl)-piperazin-1-yl]-pyridin-4-yloxy}-ethanol (0.5 g, 84%) as a solid.

Workup

  1. customThe excess TFA and HCl were evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-af86a8ecc95b4da78bd6c1a9e6224c11
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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