Sodium Carbonate → 1-[(4-Tertbutylphenyl) 4-tetrahydro pyranyloxybutyl] 4-hydroxyimino piperidine

HRID 2210830Notes

Reaction equation

HRID 2210830 reaction equation
Cl[C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH2:3][CH2:4][CH3:5].[OH:23][N:24]=[C:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:2]([O:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH2:3][CH2:4][CH2:5][N:28]2[CH2:29][CH2:30][C:25](=[N:24][OH:23])[CH2:26][CH2:27]2)=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 12849639N-Piperidin-4-ylidenehydroxylamineHCID 677823051-Chloro 1-(4-tertbutylphenyl) 1-tetrahydro pyranyloxy butane

Product 1

HCID 867490571-[(4-Tertbutylphenyl) 4-tetrahydro pyranyloxybutyl] 4-hydroxyimino piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

58.4 g of 1-chloro 1-(4-tertbutylphenyl) 1-tetrahydro pyranyloxy butane in 200 ml ethanol are heated to reflux under stirring with 20 g 4-hydroxyimino piperidine and 20 g sodium carbonate. After 20 hours reflux, the solution is concentrated to dryness then taken up with water, extracted with dried methylene chloride and concentrated to dryness under vacuum 70.5 g of pure compound are thus produced. It is recrystallized from methanol to recover 40 g of a solid having a melting point of 150°-151° C.

Workup

  1. temperatureto reflux
  2. temperatureAfter 20 hours reflux
  3. concentrationthe solution is concentrated to dryness
  4. extractionextracted with dried methylene chloride
  5. concentrationconcentrated to dryness under vacuum 70.5 g of pure compound
  6. customare thus produced
  7. customIt is recrystallized from methanol
  8. customto recover 40 g of a solid

Sources & evidence

ORD record
ord-8a42992900cd40b896bf9dc5bc6fd43a
Source dataset
uspto-grants-1995_10
Patent number
US05461059

Reaction notes

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