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

HRID 30543

Reaction equation

HRID 30543 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-67fb278fb8d946049d25207848a9308e
Source dataset
uspto-grants-2008_09
Patent number
US07423177B2

Linked notes

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