Hydroxyamine hydrochloride → HCID 86585534, compound

HRID 2414272Notes

Reaction equation

HRID 2414272 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[NH2:24][OH:25]>N1C=CC=CC=1.C(O)C>[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:21])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[N:24][OH:25])[CH:14]=2)[CH:9]([CH3:22])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22645396HCID 22645396, compound

Product 1

HCID 86585534HCID 86585534, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A solution of 1-hexyl-3,4-dimethyl-4-(3-formylphenyl)piperidine (Example 28, 80 mg, 0.27 mmol) in a mixture of pyridine (1 mL) and ethanol (1 mL) was treated with hydroxylamine hydrochloride (22 mg, 0.32 mmol) and the resulting mixture was heated at reflux for 18 hours. The solvent was evaporated in vacuo and the residual orange oil was purified by column chromatography on silica gel (10 g) eluted with a gradient of dichloromethane:methanol:0.880 ammonia (98:1:1 to 94:5:1). This gave the title compound as an oil (18 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residual orange oil was purified by column chromatography on silica gel (10 g)
  5. washeluted with a gradient of dichloromethane

Sources & evidence

ORD record
ord-edbf31404ce3480bb1db95df365867c3
Source dataset
uspto-grants-2004_11
Patent number
US06812236B2

Reaction notes

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