tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate → tert-Butyl{1-[2-(6-chloro-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 255372Notes

Reaction equation

HRID 255372 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N+:10]([O-])=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]3)[C:6]=2[CH:29]=1>C(O)(=O)C.O.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:17][CH2:16]3)[C:6]=2[CH:29]=1

Participants

5

Reactant 1

HCID 86642661tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 86664539tert-Butyl{1-[2-(6-chloro-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamateYield 16%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 206) (0.43 g) in acetic acid (8 mL) and water (2 mL) was added zinc dust (0.50 g). After 30 minutes, the solution was filtered and the filtrate concentrated. The residue was then treated with potassium ferricyanide (1.0 g) in water (20mL). After 2 hours, the reaction was diluted with ethyl acetate. The aqueous layer was collected, the pH adjusted with solid Na2CO3 and extracted with ethyl acetate. The combined organic washes were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel with 0-25% acetone in dichloromethane to yield 66 mg of the product.

Workup

  1. filtrationthe solution was filtered
  2. concentrationthe filtrate concentrated
  3. additionThe residue was then treated with potassium ferricyanide (1.0 g) in water (20mL)
  4. waitAfter 2 hours
  5. additionthe reaction was diluted with ethyl acetate
  6. customThe aqueous layer was collected
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic washes were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel with 0-25% acetone in dichloromethane

Sources & evidence

ORD record
ord-d54c2a52c7674f99a37d975eea235479
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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