3-Methoxyaniline → HCID 22037924, compound

HRID 1790529Notes

Reaction equation

HRID 1790529 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[CH:18]=1.[C:24]([N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)(=[O:26])[CH3:25].[OH-].[Na+]>ClC(Cl)C.C(OCC)(=O)C.C(O)(=O)C>[C:24]([N:27]1[CH2:32][CH2:31][CH:30]([NH:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH3:15])[CH:18]=2)[CH2:29][CH2:28]1)(=[O:26])[CH3:25]

Participants

8

Reactant 4

HCID 108243-MethoxyanilineHCID 14798Sodium HydroxideHCID 122563N-Acetyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22037924HCID 22037924, compoundYield 88.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, sodium triacetoxyborohydride (12.0 g) was added to a liquid mixture of m-anisidine (4.40 g), 1-acetylpiperidin-4-one (5.0 g) and acetic acid (8 ml) in dichloroethane (80 ml). Then the reaction mixtures were stirred at room temperature overnight. The reaction mixtures were diluted with ethyl acetate (200 ml) and a 5 N aqueous solution (35 ml) of sodium hydroxide was added thereto. The organic layer was separated, washed successively with water and brine and dried over magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/hexane system) to give the title compound (7.80 g) as a brown oil (yield: 87.9%).

Workup

  1. customThen the reaction mixtures
  2. customThe reaction mixtures
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporating the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-41acfd82f73d47af87ceb039e051c050
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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