Potassium Carbonate → HCID 15940788, compound

HRID 657658Notes

Reaction equation

HRID 657658 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[N:26]1([CH2:25][CH2:24][CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][N+:11]([O-:14])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 178526241HCID 178526241, compound

Product 1

HCID 15940788HCID 15940788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A A mixture of 4-(4-hydroxyphenyl)pyridine 1-oxide (250 mg), potassium carbonate (560 mg) and 1-(3-chloropropyl)piperidine, hydrochloride in N,N-dimethylformamide (10 mL) is heated at a temperature close to 65° C. overnight, then cooled back to room temperature and filtered. The filtrate is concentrated under reduced pressure and the residue purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10). Fraction containing the compound are pooled and concentrated under reduced pressure. Crude base is diluted with ethanol, oxalic acid (28 mg) is added and solvent removed under reduced pressure to give 40 mg of 4-[4-(3-piperidino-propoxy)phenyl]pyridine 1-oxide, oxalate as a viscous yellow product.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 65° C. overnight
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 90/10)
  6. additionFraction containing the compound
  7. concentrationconcentrated under reduced pressure
  8. additionCrude base is diluted with ethanol, oxalic acid (28 mg)
  9. additionis added
  10. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-1527f40cf88c4327b032d18f3a4ec966
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…