Acetic Acid → HCID 59507768, compound

HRID 1512123Notes

Reaction equation

HRID 1512123 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:23][C:24]([CH3:26])=O.C([BH3-])#N.[Na+]>CO>[CH:24]([N:13]1[CH2:14][CH2:15][CH:10]([O:9][C:8]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:7]=2[O:6][CH3:5])[CH2:11][CH2:12]1)([CH3:26])[CH3:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180Acetone2×HCID 5003444Sodium cyanoborohydride2×HCID 550361544-(2-Methoxy-4-nitrophenoxy)piperidine

Product 1

HCID 59507768HCID 59507768, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10% acetic acid in methanol was added 4-(2-methoxy-4-nitrophenoxy)piperidine (148 mg, 0.59 mmol, 1 eq), anhydrous acetone (5 eq), and sodium cyanoborohydride (1.5 eq). The solution was stirred at room temperature for 24 h. Additional anhydrous acetone (5 eq) and sodium cyanoborohydride (1.5 eq) were added and the reaction was stirred for 24 h. The solvent was evaporated, the residue was brought to pH 10 with aqueous sodium carbonate and extracted with EtOAc. The organic layer was washed with water, brine, dried with magnesium sulfate and evaporated to afford 1-isopropyl-4-(2-methoxy-4-nitrophenoxy)piperidine as a yellow oil (163 mg, 97%). LC/MS (m/z): 295.2 (MH+), Rt 1.96 minutes.

Workup

  1. stirringthe reaction was stirred for 24 h
  2. customThe solvent was evaporated
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-34437dc11089452da06f322c3ff06177
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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