Water → 4-[4-(t-Butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-Oxide

HRID 25039

Reaction equation

HRID 25039 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([OH:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:23]=[CH:22][N+:21]([O-:24])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].O>C(O)CC(C)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([OH:16])[CH2:11][CH2:12][N:13]([C:18]2[CH:23]=[CH:22][N+:21]([O-:24])=[CH:20][CH:19]=2)[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 707244-chloropyridine N-oxideHCID 516892Sodium BicarbonateHCID 10868112tert-butyl N-((4-hydroxypiperidin-4-yl)methyl)carbamate

Product 1

HCID 110346584-[4-(t-Butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-OxideYield 36.8%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

To a suspension in isoamyl alcohol (35 ml) of conventionally known compounds: 4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine (2.00 g) and 4-chloropyridine 1-oxide (1.12 g), was added sodium hydrogencarbonate (1.75 g) and the mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool and water was added thereto. The reaction mixture was extracted with methylene chloride and the organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1) to obtain the title compound (1.03 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. extractionThe reaction mixture was extracted with methylene chloride
  5. washthe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

Sources & evidence

ORD record
ord-784990b1458d4facbd2c0e6fab5babbd
Source dataset
uspto-grants-2005_02
Patent number
US06858599B2

Linked notes

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