Sodium Hydroxide → HCID 178461427, compound

HRID 657665Notes

Reaction equation

HRID 657665 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][C@H:20]([CH3:24])[CH2:19]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH-:25].[Na+]>CO>[OH:25][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][C@H:20]([CH3:24])[CH2:19]3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 576720232-chloro-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine

Product 1

HCID 178461427HCID 178461427, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A A mixture of 2-chloro-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine (345 mg), sodium hydroxide (288 mg) and methanol (1.55 mL) is heated overnight at a temperature close to 170° C. in a sealed tube. The mixture is cooled to a temperature close to 0° C. and neutralized with a cold concentrated aqueous hydrochloric solution. Methanol (1.3 mL) is added and the precipitate separated by filtration. The filtrate is concentrated under reduced pressure and purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 80/20). Fraction containing the expected product are pooled and concentrated under reduced pressure. The crude base is dissolved in ethanol; oxalic acid (118 mg) is added followed by diethyl ether. The precipitate that appears is separated by filtration, washed with ethanol and dried under reduced pressure to give 110 mg of 2-hydroxy-4-(4-{3-[(3S)-3-methylpiperidin-1-yl]propoxy}phenyl)pyridine, oxalate as a white powder melting at 110° C.

Workup

  1. temperatureis heated overnight at a temperature
  2. customclose to 170° C. in a sealed tube
  3. temperatureThe mixture is cooled to a temperature
  4. customclose to 0° C.
  5. customthe precipitate separated by filtration
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. custompurified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 80/20)
  8. additionFraction containing the expected product
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe crude base is dissolved in ethanol
  11. additionoxalic acid (118 mg) is added
  12. customThe precipitate that appears is separated by filtration
  13. washwashed with ethanol
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-c14c871b3df14dedb7e8de6c10657d77
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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