(E)-2-chloro-N,N-diethyl-4-(prop-1-enyl)benzamide → HCID 69053181, compound

HRID 2100587Notes

Reaction equation

HRID 2100587 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH3:17])[CH:12]=[CH:11][C:3]=1[C:4]([N:6]([CH2:9][CH3:10])[CH2:7][CH3:8])=[O:5].[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][CH3:17])[CH:12]=[CH:11][C:3]=1[C:4]([N:6]([CH2:7][CH3:8])[CH2:9][CH3:10])=[O:5]

Participants

5

Reactant 2

HCID 69061192(E)-2-chloro-N,N-diethyl-4-(prop-1-enyl)benzamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 69053181HCID 69053181, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To the crude (E)-2-chloro-N,N-diethyl-4-(prop-1-enyl)benzamide in 100 mL of absolute ethanol was added 10% Pd/C catalyst (1 g). The mixture was stirred under 1 atm of hydrogen, maintained by a balloon, for 18 h. Starting material still remained and so additional 10% Pd/C (0.5 g) was added and the reaction was charged with a fresh hydrogen balloon and stirred and additional 24 h. The reaction mixture was filtered through a pad of Celite and concentrated. The residue was purified by flash chromatography (230-400 mesh silica gel, elution with 8:1 to 6:1 hexane/EtOAc) to afford 2.15 g (67%) of the title compound. 1H NMR (CDCl3): δ 7.12 (d, 1H, J=1.1 Hz), 7.09 (d, 1H, J=7.7 Hz), 7.02 (dd, 1H, J=1.6, 7.7 Hz), 3.75-3.68 (m, 1H), 3.32-3.25 (m, 1H), 3.11-3.06 (m, 2H), 2.50 (t, 2H, J=7.7 Hz), 1.60-1.52 (m, 2H), 1.19 (t, 3H, J=7.1 Hz), 0.99 (t, 3H, J=7.1 Hz), 0.87 (t, 3H, J=7.4 Hz). LRMS (ESI): 254.10/256.10 (M+H)+.

Workup

  1. temperaturemaintained by a balloon, for 18 h
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (230-400 mesh silica gel, elution with 8:1 to 6:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-1a13d5070aa449b79af0e172dfd693b4
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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