Hydroxylamine, O-ethyl- → HCID 11952101, compound

HRID 507863Notes

Reaction equation

HRID 507863 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:12]2[CH2:17][CH2:16][N:15]([CH:18]3[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH2:25]([O:27][NH2:28])[CH3:26].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH2:25]([O:27][N:28]=[C:21]1[CH2:22][CH2:23][CH:18]([N:15]2[CH2:14][CH2:13][CH:12]([N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:9](=[O:11])[CH3:10])[CH2:17][CH2:16]2)[CH2:19][CH2:20]1)[CH3:26]

Participants

5

Reactant 3

HCID 69357Hydroxylamine, O-ethyl-HCID 516892Sodium BicarbonateHCID 59434297HCID 59434297, compound

Product 1

HCID 11952101HCID 11952101, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-fluorophenyl)-N-(1-(4-oxocyclohexyl)piperidin-4-yl)acetamide (100 mg; 0.3 mmol; 1 eq.) was dissolved in pyridine (2 mL). O-ethylhydroxylamine (22 mg, 0.36 mmol; 1.2 eq.) was added. The solution was heated to 80° C. for 30 min. Saturated NaHCO3 (10 mL) was added and the solution was extracted with EtOAc (2×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by reversed-phase HPLC (2-99% CH3CN/H2O gradient with 0.05% TFA) to provide the desired product. LC/MS m/z 333.2, Retention time=1.79; 10-99% CH3CN/H2O gradient with 0.05% TFA).

Workup

  1. extractionthe solution was extracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by reversed-phase HPLC (2-99% CH3CN/H2O gradient with 0.05% TFA)

Sources & evidence

ORD record
ord-b31503b9e1864c2880703091ac6eb792
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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