Hydroxylamine → HCID 21708613, compound

HRID 1376495Notes

Reaction equation

HRID 1376495 reaction equation
[C:1](O)(=O)[C:2]([OH:4])=[O:3].Cl[C:8]1([C:16]2[C:17](Cl)=[N:18]S[N:20]=2)[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1.[NH2:22][OH:23].[O:24]=P(Cl)(Cl)Cl.[OH-:29].[Na+]>CO.O>[C:2]([OH:4])(=[O:3])/[CH:1]=[CH:16]/[C:17]([OH:24])=[O:29].[NH2:18][C:17]1[C:16]([CH:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[N:20][O:23][N:22]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 21708661HCID 21708661, compound

Product 1

HCID 21708613HCID 21708613, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of crude (1-azabicyclo[2.2.21octan-3-yl)hydroxyiminoacetonitrile (10 g, max. 29 mmol) (example 1 C) in methanol (50 ml) was added a methanol solution of hydroxylamine (prepared from NH2OH, HCl (4.2 g, 60 mmol) in methanol (60 ml) and sodium (1.38 g, 60 mmol) in methanol (60 ml)). The reaction mixture was stirred at 40° C. for 18 h and evaporated to give the crude amide oxime derivative. The residue was treated with excess of POCl3 at 45° C. for 18 h. Water and sodium hydroxide was added to obtain alkaline pH and the aqueous mixture extracted with chloroform. The combined organic phases were dried and evaporated to give the free base of the title compound as a solid (yield 570 mg). MS: M+ : 194. Crystallization as the fumarate salt from isopropanol gave the title compound (110 mg) (Compound 66), M.p. 60°-75° C.

Workup

  1. customevaporated
  2. customto give the crude amide oxime derivative
  3. customto obtain alkaline pH
  4. extractionthe aqueous mixture extracted with chloroform
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-a72d37ab49024f9683927ee459e9c367
Source dataset
uspto-grants-1997_09
Patent number
US05663182

Reaction notes

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