Hydroxyamine hydrochloride → HCID 73865530, compound

HRID 1456305Notes

Reaction equation

HRID 1456305 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10][C:9]2=O)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][C:12](=[O:14])[CH2:11][CH2:10][C:9]2=[N:17][OH:18])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22106486HCID 22106486, compound

Product 1

HCID 73865530HCID 73865530, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6-(3-bromo-phenyl)-piperidin-2,5-dione (38.2 g) and hydroxylamine hydrochloride (19.8 g) in pyridine (300 ml) was stirred at room temperature under nitrogen. After 4 h the mixture was evaporated in vacuo. The crude mixture was partitioned between chloroform (200 ml) and water (200 ml) then was basified by the addition of 8% sodium bicarbonate solution (~300 ml). The mixture was extracted with chloroform (300 ml×2). The combined organic extracts were washed with saturated brine and evaporated in vacuo. Trituration with ether gave the title compound as a pale yellow solid (34.9 g).

Workup

  1. customAfter 4 h the mixture was evaporated in vacuo
  2. customThe crude mixture was partitioned between chloroform (200 ml) and water (200 ml)
  3. additionthen was basified by the addition of 8% sodium bicarbonate solution (~300 ml)
  4. extractionThe mixture was extracted with chloroform (300 ml×2)
  5. washThe combined organic extracts were washed with saturated brine
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-c2cd2df7e3b849e8bc31c813cbdfb289
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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