Hydroxyamine hydrochloride → HCID 23084750, compound

HRID 1783316Notes

Reaction equation

HRID 1783316 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]#[N:16])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].COC(N1CCC(C(C(C2C=CC=CC=2)C#N)=O)CC1)=O.Cl.[NH2:45][OH:46].C([O-])(=O)C.[Na+]>O.C(O)C>[NH2:16][C:15]1[O:46][N:45]=[C:12]([CH:9]2[CH2:10][CH2:11][N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]2)[C:14]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 23084749HCID 23084749, compoundHCID 23084830HCID 23084830, compound

Product 1

HCID 23084750HCID 23084750, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture (1:1, 17.5 g) of α-(1-ethoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile and α-(1-methoxycarbonylpiperidin-4-yl)carbonylphenylacetonitrile, hydroxylamine hydrochloride (5.63 g) and sodium acetate (13.1 g) were suspended in water (20 mL) and ethanol (160 mL), and the suspension was heated under reflux for 6 hrs. After the completion of the reaction, the mixture was cooled to room temperature. The insoluble material was filtered off using ethanol, and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, and washed with water and saturated brine. The chloroform layer was concentrated under reduced pressure, and the obtained crystals were purified by column chromatography (n-hexane:ethyl acetate=3:1→1:1) to give a mixture (1:1, 7.02 g) of 5-amino-3-(1-ethoxycarbonylpiperidin-4-yl)-4-phenylisoxazole and 5-amino-3-(1-methoxycarbonylpiperidin-4-yl)-4-phenylisoxazole as pale-yellow crystals.

Workup

  1. temperatureunder reflux for 6 hrs
  2. customAfter the completion of the reaction
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with water and saturated brine
  7. concentrationThe chloroform layer was concentrated under reduced pressure
  8. customthe obtained crystals were purified by column chromatography (n-hexane:ethyl acetate=3:1→1:1)

Sources & evidence

ORD record
ord-d6d41f9e20934b8ea0055f3cf62db671
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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