Dimethylamine → N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide

HRID 1894748Notes

Reaction equation

HRID 1894748 reaction equation
Br[CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4].[CH3:17][NH:18][CH3:19].CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl.CO>[CH3:17][N:18]([CH3:19])[CH:2]([CH2:15][CH3:16])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 63386157N-[4-(2-bromobutanoyl)phenyl]acetamide

Product 1

HCID 86681892N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of N-(4-(2-bromobutanoyl)phenyl)acetamide (4.80 g, 16.9 mmol) in 30 mL CHCl3 and 30 mL MeOH was treated with 16.9 mL dimethylamine in MeOH (2M, 33.8 mmol) and DIPEA (2.90 mL, 16.9 mmol). After stirring at rt for 48 hr, the mixture was concentrated in vacuo and the residue partitioned between DCM and saturated NaHCO3. The aqueous phase was extracted with DCM three times. The combined organic extracts were dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluting with 6% MeOH (2N NH3)/DCM to provide N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide as a light brown oil. MS ESI: m/z 249.19 [M+1+].

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue partitioned between DCM and saturated NaHCO3
  3. extractionThe aqueous phase was extracted with DCM three times
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 6% MeOH (2N NH3)/DCM

Sources & evidence

ORD record
ord-f32815d5d93445389764970dc56bc002
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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