Acetic Acid → 1-Isopropyl-4-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-piperidine

HRID 2211619Notes

Reaction equation

HRID 2211619 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[C:8]([CH:17]=1)[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([O-:3])=[O:2].[CH3:25][C:26]([CH3:28])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[CH:26]([N:14]1[CH2:15][CH2:16][CH:11]([CH2:10][O:9][C:8]2[CH:17]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[C:18]([F:24])([F:23])[C:19]([F:20])([F:21])[F:22])[CH2:12][CH2:13]1)([CH3:28])[CH3:25]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180Acetone2×HCID 5049666Sodium triacetoxyborohydrideHCID 219593894-(3-Nitro-6-pentafluoroethyl-phenoxymethyl)-piperidine

Product 1

HCID 219594781-Isopropyl-4-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-piperidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolved 4-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-piperidine (646 mg) in 1,2-dichloroethane (6.4 mL), then added acetone (136 μL), NaBH(OAc)3 (541 mg) and finally AcOH (105 μL). Stirred the cloudy yellow solution under N2 at RT overnight. Added another 130 μL acetone and stirred at RT over weekend. Quenched the reaction with 30 mL N NaOH/H2O and stirred 10 min. Extracted with Et2O and the organic layer was brine-washed, dried over Na2SO4, filtered and concentrated in vacuo. Dried under high vacuum for several h to obtain 1-isopropyl-4-(5-nitro-2-pentafluoroethyl-phenoxymethyl)-piperidine as a yellow orange solid.

Workup

  1. stirringstirred at RT over weekend
  2. customQuenched
  3. customthe reaction with 30 mL N NaOH/H2O
  4. stirringstirred 10 min
  5. extractionExtracted with Et2O
  6. washwashed
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customDried under high vacuum for several h

Sources & evidence

ORD record
ord-e153508e229b49809808e456723f0c05
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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