Potassium Carbonate → 3-(N,N-diethylaminopropoxy)butyranilide

HRID 503667Notes

Reaction equation

HRID 503667 reaction equation
S([O-])(=O)(=O)C.[CH2:6]([N:8]([CH:11](O)[CH2:12][CH3:13])[CH2:9][CH3:10])[CH3:7].[C:15]([NH:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1)(=[O:19])[CH2:16][CH2:17][CH3:18].C([O-])([O-])=[O:29].[K+].[K+]>CN(C=O)C>[CH2:6]([N:8]([CH2:11][CH2:12][CH2:13][O:29][CH:17]([CH3:18])[CH2:16][C:15]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19])[CH2:9][CH3:10])[CH3:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 30688Butyranilide, 3'-hydroxy-HCID 85257MethanesulfonateHCID 5256659Diethylamino-propanol

Product 1

HCID 684282403-(N,N-diethylaminopropoxy)butyranilideYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mesylate of N,N-diethylaminopropanol (6 mmol), prepared as described in Example 18 above, was mixed with 3-butyramidophenol (5.0 mmol), and K2CO3 (10 mmol) in anhydrous DMF (10 mL) and the reaction is performed following general procedure B. The crude product is purified using silica gel column chromatography 5% MeOH/DCM as eluent to yield 3-(N,N-diethylaminopropoxy)butyranilide (1.3 g).

Workup

  1. customThe crude product is purified

Sources & evidence

ORD record
ord-b16b596d33f145d9bb5ca5ecfd40c02f
Source dataset
uspto-grants-2010_08
Patent number
US07776919B2

Reaction notes

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