Hydroxyamine hydrochloride → HCID 86733172, compound

HRID 267979Notes

Reaction equation

HRID 267979 reaction equation
[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].Cl.[NH2:39][OH:40]>N1C=CC=CC=1>[ClH:1].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[N:39][OH:40])[CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([C:23]([OH:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21552950HCID 21552950, compound

Product 1

HCID 86733172HCID 86733172, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 15 g (0.028 mole) of 4'-tert-butyl-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone hydrochloride and 15 g of hydroxylamine hydrochloride in 120 ml of pyridine in heated on a steam bath for about 5 hours after which the pyridine is removed at reduced pressure. The remaining residue is dissolved in methanol and added to excess iced 10% HCl. The resulting solid is filtered, washed with water, and recrystallized from isopropyl alcohol to give 4'-tert-butyl-5-[4-(α-hydroxy-α-phenylbenzyl)piperidino]valerophenone oxime hydrochloride.

Workup

  1. customis removed at reduced pressure
  2. dissolutionThe remaining residue is dissolved in methanol
  3. additionadded to excess iced 10% HCl
  4. filtrationThe resulting solid is filtered
  5. washwashed with water
  6. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-67211c16b4c04b74b6210591aab9f735
Source dataset
uspto-grants-1976_03
Patent number
US03946022

Reaction notes

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