Methyl morpholine oxide → N-(1-(4-formylphenyl)piperidin-4-yl)acetamide

HRID 591610Notes

Reaction equation

HRID 591610 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66745026N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)acetamide

Product 1

HCID 86662017N-(1-(4-formylphenyl)piperidin-4-yl)acetamideYield 74.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)acetamide (0.380 g, 1.53 mmol), TPAP (0.026 g, 0.08 mmol), NMO (0.268 g, 2.30 mmol), and molecular sieves (3 Angstrom, 0.300 g) in CH2Cl2 was stirred at room temperature for 19 hours. The mixture was filtered through Celite, concentrated, and purified by flash chromatography on silica gel, eluting with 100% ethyl acetate to 10% MeOH/ethyl acetate, to afford N-(1-(4-formylphenyl)piperidin-4-yl)acetamide as a white solid (0.280 g, 74%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. custompurified by flash chromatography on silica gel
  4. washeluting with 100% ethyl acetate to 10% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-14d9c13f658f426fb4af7cf1980d2a93
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…