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

HRID 591621Notes

Reaction equation

HRID 591621 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:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[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[CH2:10][CH2:11][CH:12]([NH:15][C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14]2)=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66745757N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide

Product 1

HCID 86662018N-(1-(4-formylphenyl)piperidin-4-yl)benzamideYield 32.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(4-(hydroxymethyl)phenyl)piperidin-4-yl)benzamide (1.1 g, 3.5 mmol) in CH2Cl2 (250 mL) was added TPAP (0.123 g, 0.35 mmol) and NMO (0.623 g, 5.3 mmol). After 1 hour, the mixture was filtered through Celite, concentrated, and purified by silica gel chromatography, eluting with 30% ethyl acetate/hexanes to 100% ethyl acetate, to afford N-(1-(4-formylphenyl)piperidin-4-yl)benzamide as a white solid (0.350 g, 32%).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography
  4. washeluting with 30% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record
ord-57908674aba840a289fd5184994ea452
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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