Acetic Acid → HCID 59507768, compound

HRID 1043798Notes

Reaction equation

HRID 1043798 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. Reaction is 85% complete. Charged additional anhydrous acetone (5 eq) and sodium cyanoborohydride (1.5 eq) and stirred for 24 h. The solvent was evaporated, the residue brought to pH=10 with 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. customReaction
  2. stirringstirred for 24 h
  3. customThe solvent was evaporated
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-108dd4aa589a45ef96c746cbc9f2f135
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

Loading…