Sodium Hydroxide → HCID 59438206, compound

HRID 604319Notes

Reaction equation

HRID 604319 reaction equation
Cl.Cl.[N:3]1([C:9]2[C:10]([N:15]3[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[OH-].[Na+]>[Cl-].[Na+]>[N:3]1([C:9]2[C:10]([N:15]3[CH2:16][CH2:17][CH:18]([OH:21])[CH2:19][CH2:20]3)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66601607HCID 66601607, compound

Product 1

HCID 59438206HCID 59438206, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

Dissolve 1-(3-(piperazin-1-yl)pyridin-2-yl)piperidin-4-ol dihydrochloride (281.0, 0.838 mol) in saturated aqueous sodium chloride solution (2.45 liters). Add 2 M NaOH (˜1 L) to bring the pH to 11.3. Extract the mixture three times with DCM (3×2.04 L). Dry the combined organics over sodium sulfate, filter, and evaporate solvent on a rotary evaporator with a nitrogen bleed to obtain a foam. When the foam is stable, further dry the material for 2 to 3 hr. at 50° C. under vacuum to provide 1-(3-(piperazin-1-yl)pyridin-2-yl)piperidin-4-ol (207.5 g, 94.1%). 1H NMR 300 MHz (CDCl3) δ 7.923 (dd, J=3.1 Hz, 1H), 7.10 (d, J=6.3 Hz, 1H), 6.815 (m, 1H), 4.040 (m, 2H), 3.840 (m, 1H), 3.048 (bs, 8H), 2.898 (m, 2H), 2.028 (m, 2H), 1.862 (s, 2H ??), 1.634 (m, 2H).

Workup

  1. extractionExtract the mixture three times with DCM (3×2.04 L)
  2. dry with materialDry the combined organics over sodium sulfate
  3. filtrationfilter
  4. customevaporate solvent
  5. customon a rotary evaporator with a nitrogen
  6. customto obtain a foam
  7. customfurther dry the material for 2 to 3 hr

Sources & evidence

ORD record
ord-5804d86f92c04fb68d34118ab3462171
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

Loading…