Triethylamine → tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylate

HRID 1197490Notes

Reaction equation

HRID 1197490 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:16][OH:17].C(N(CC)CC)C>CO>[C:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:16][OH:17])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 15462924tert-Butyl 4-(hydroxyimino)piperidine-1-carboxylateYield 63.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.5 g (77.6 mmol) of N-Boc-4-piperidone was refluxed for one hour in methanol in the presence of 7.0 g (100.8 mmol) of hydroxylamine hydrochloride and 14.1 ml (100.8 mmol) of triethylamine. Then, methanol was distilled off, and the residue was thoroughly washed with water in chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 10.6 g of N-Boc-4-hydroxyiminopiperidine as white powder.

Workup

  1. distillationThen, methanol was distilled off
  2. washthe residue was thoroughly washed with water in chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9442df58577645f18da8275ef4bf7b98
Source dataset
uspto-grants-1994_01
Patent number
US05276041

Reaction notes

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