Potassium Carbonate → 4-(N,N-diethylaminopropoxy)butyranilide

HRID 30541

Reaction equation

HRID 30541 reaction equation
S(Cl)(C)(=O)=O.[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:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1)(=[O:19])[CH2:16][CH2:17][CH3:18].C([O-])([O-])=[O:29].[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH2:6]([N:8]([CH2:11][CH2:12][CH2:13][O:29][CH2:18][CH2:17][CH2:16][C:15]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH2:9][CH3:10])[CH3:7]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 668744'-HydroxybutyranilideHCID 5256659Diethylamino-propanol

Product 1

HCID 684301664-(N,N-diethylaminopropoxy)butyranilideYield 95.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Mesyl Chloride (6.0 mmol) was added dropwise at 0° C. to a stirred solution of N,N-diethylaminopropanol (6.0 mmol), TEA (6.0 mmol) in anhydrous DCM (6 mL), and the mixture was stirred at the same temperature for 10 min, and at room temperature for additional 1 h. After the removal of the solvent in vacuo, the solid residue was mixed with 4-butyramidophenol (5.0 mmol), and K2CO3 (10 mmol) in anhydrous DMF (10 mL), following general procedure B. The crude product is purified using silica gel column chromatography 5% MeOH/DCM as eluent to yield 4-(N,N-diethylaminopropoxy)butyranilide (1.4 g).

Workup

  1. waitat room temperature for additional 1 h
  2. customAfter the removal of the solvent in vacuo
  3. customThe crude product is purified

Sources & evidence

ORD record
ord-955a88f5c99c4573aeed67c119de73a3
Source dataset
uspto-grants-2008_09
Patent number
US07423177B2

Linked notes

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