Hydroxyamine hydrochloride → 4'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone oxime

HRID 267980Notes

Reaction equation

HRID 267980 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:33])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1.Cl.[NH2:36][OH:37]>N1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[N:36][OH:37])[CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:33])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 215529524'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone hydrochloride

Product 1

HCID 867331744'-Fluoro-5-[4-(alpha-hydroxy-alpha-phenylbenzyl)piperidino]valerophenone oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 15 g (0.033 mole) of 4'-fluoro-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride and 15 g of hydroxylamine hydrochloride in 120 ml of pyridine is stirred on a steam bath for about 4 hours then cooled to room temperature. The pyridine is removed at reduced pressure on a steam bath, and the residue is triturated with a dilute sodium hydroxide solution and extracted with chloroform. The chloroform extract is washed with water, dried over magnesium sulfate, filtered and concentrated to a residue which is triturated with hexane. The resulting solid is filtered off and recrystallized from ethanol to give 4'-fluoro-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone oxime.

Workup

  1. customThe pyridine is removed at reduced pressure on a steam bath
  2. customthe residue is triturated with a dilute sodium hydroxide solution
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washis washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a residue which
  9. customis triturated with hexane
  10. filtrationThe resulting solid is filtered off
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8a092aa9f0444080907d91cc8e27262d
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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