Hydroxylamine → HCID 18919633, compound

HRID 1290888Notes

Reaction equation

HRID 1290888 reaction equation
[NH2:1][OH:2].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][C:14](=O)[CH2:15]3)[CH2:5][CH2:4]1>C(O)C>[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][C:14](=[N:1][OH:2])[CH2:15]3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 13741757HCID 13741757, compound

Product 1

HCID 18919633HCID 18919633, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 22.2 ml of 50% hydroxylamine aqueous solution was added to a solution of 40.0 g of 8-(2-morpholinoethyl)-8-azabicyclo[3.2.1]octan-3-one in 200 ml of ethanol, the mixture was stirred at room temperature for an hour. The solvent was distilled off and toluene was added followed by azeotropic distillation. After the solvent was distilled off, the residue was purified by silica gel column chromatography (chloroform:NH3 -saturated methanol=20:1) to give 32.8 g of 8-(2-morpholinoethyl)-8-azabicyclo[3.2.1]octan-3-one oxime.

Workup

  1. distillationThe solvent was distilled off
  2. additiontoluene was added
  3. distillationfollowed by azeotropic distillation
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (chloroform:NH3 -saturated methanol=20:1)

Sources & evidence

ORD record
ord-be9e2a65c30c4db7912db12a01f27bc9
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Reaction notes

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