Sodium Hydroxide → beta-Piperidinopropiophenone oxime

HRID 35012

Reaction equation

HRID 35012 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[NH2:19][OH:20].C(=O)([O-])O.[Na+].[OH-].[Na+]>O.[Ag]>[N:2]1([CH2:8][CH2:9][C:10](=[N:19][OH:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 701713-Piperidinopropiophenone hydrochlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 23906289beta-Piperidinopropiophenone oximeYield 74.8%

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 962WaterSolvent2×

Procedure

In 470 ml of water were dissolved 60.2 g of β-piperidinopropiophenone hydrochloride and 18.1 g of hydroxylamine hydrochloride. To this solution was added portionwise 21.9 g of sodium hydrogencarbonate. After the whole amount was added, the mixture was stirred overnight. To the stirred mixture was then added an aqueous solution of 14.2 g of sodium hydroxide in 47 ml of water. Thus obtained mixture was well stirred and allowed to stand for 2 hours to produce a white precipitate. The precipitate was collected by filtration and washed successively with two portions of 200 ml of water and ethanol. The washed precipitate was dried to obtain a white solid. The solid was then recrystallized from methanol to obtain 41.2 g (yield: 74.8%) of the subject compound as a silver-white scaly product.

Workup

  1. additionAfter the whole amount was added
  2. stirringThus obtained mixture was well stirred
  3. waitto stand for 2 hours
  4. customto produce a white precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washwashed successively with two portions of 200 ml of water and ethanol
  7. customThe washed precipitate was dried
  8. customto obtain a white solid
  9. customThe solid was then recrystallized from methanol

Sources & evidence

ORD record
ord-e9c738adc29e404d9db764e041f0902d
Source dataset
uspto-grants-1988_08
Patent number
US04764617

Linked notes

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