1-Benzyl-4-piperidone → 1-Benzyl-4-piperidone oxime

HRID 1979636

Reaction equation

HRID 1979636 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[N:16][OH:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 703651-Benzyl-4-piperidone oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Following a procedure of P. Brookes, et al., J. Chem. Soc., 3165 (1957), 1-benzyl-4-piperidinone (44.6 g, 0.234 mol) and hydroxylamine hydrochloride (14.0 g, 0.201 mol) are added to 140 ml of dry pyridine and the resulting mixture is heated to 100° C. in an oil bath for 3 hours. The resulting solid is cooled overnight, filtered and crystallized from 1 liter of ethanol. The product is collected as colorless needles, 38.17 g, in two groups with melting point of 225°-237° C., decomposed depending upon the rate of heating.

Workup

  1. temperatureThe resulting solid is cooled overnight
  2. filtrationfiltered
  3. customcrystallized from 1 liter of ethanol
  4. customThe product is collected as colorless needles, 38.17 g, in two groups with melting point of 225°-237° C.
  5. temperatureof heating

Sources & evidence

ORD record
ord-166b407e750b4f909d55a9ef699987c2
Source dataset
uspto-grants-1984_11
Patent number
US04481360

Linked notes

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