Hydroxyamine hydrochloride → HCID 67684354, compound

HRID 342207Notes

Reaction equation

HRID 342207 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH:25]3[CH2:27][CH2:26]3)[CH3:24])=[CH:12][C:11]=2F)=O)=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].C([O-])(=O)C.[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH:25]4[CH2:27][CH2:26]4)[CH3:24])=[CH:12][C:11]=3[O:31][N:30]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 18434247HCID 18434247, compound

Product 1

HCID 67684354HCID 67684354, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 0.15 g of (4-bromo-phenyl)-[4-[6-(cyclopropyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl]-methanone, 0.17 g of hydroxylamine.hydrochloride and 0.20 g of sodium acetate in 14 ml of ethanol is heated to 90° C. for 32 hrs. and then concentrated. The residue (containing the oxime corresponding to the starting ketone) is taken up in 50 ml of methylene chloride and washed with saturated aqueous sodium hydrogen carbonate solution and sodium chloride solution. The organic phase is dried and evaporated. The residue is dissolved in 15 ml of DMA and treated with 0.22 g of potassium carbonate. The mixture is heated at 130° C. for 5 hrs. For the working-up, the reaction mixture is filtered, the filtrate is concentrated and the residue is purified by chromatography (silica gel, toluene/acetone/triethylamine 92:7:1). There is obtained 0.077 g of [6-[3-(4-bromo-phenyl)-benzo[d]isoxazol-6-yloxy]hexyl]-cyclopropyl-methyl-amine which is converted into the fumarate, MS: m/e 443 (M+H+, 1 Br).

Workup

  1. concentrationand then concentrated
  2. additionThe residue (containing the oxime corresponding to the starting ketone)
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and sodium chloride solution
  4. customThe organic phase is dried
  5. customevaporated
  6. dissolutionThe residue is dissolved in 15 ml of DMA
  7. additiontreated with 0.22 g of potassium carbonate
  8. temperatureThe mixture is heated at 130° C. for 5 hrs
  9. filtrationthe reaction mixture is filtered
  10. concentrationthe filtrate is concentrated
  11. customthe residue is purified by chromatography (silica gel, toluene/acetone/triethylamine 92:7:1)

Sources & evidence

ORD record
ord-70dcaf653e1e4b2ab4f92705f72b58f4
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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