Methyl Ethyl Ketone → HCID 20550955, compound

HRID 1447421Notes

Reaction equation

HRID 1447421 reaction equation
[CH3:1][CH:2]([NH2:11])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH:13]([CH3:24])[C:14]([C:16]1[S:20][CH:19]=[C:18]([C:21]([NH2:23])=[O:22])[CH:17]=1)=[O:15].CC(=O)CC>CCOC(C)=O>[CH3:1][CH:2]([N:11]=[C:13]([CH3:24])[C:14]([C:16]1[S:20][CH:19]=[C:18]([C:21]([NH2:23])=[O:22])[CH:17]=1)=[O:15])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 311601-Methyl-3-phenylpropylamineHCID 20550944HCID 20550944, compound

Product 1

HCID 20550955HCID 20550955, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methyl-3-phenylpropylamine (9.0 g) and 5-(2-bromo-1-oxopropyl)thiophene-3-carboxamide (7.6 g) was stirred for 2 h; butanone (75 ml) was added and stirring continued for 48 h. The resulting mixture was filtered and the filtrate evaporated to small volume (ca. 30 ml) and added to vigorously stirred light petroleum (b.p. 60°-80°: 500 ml) to precipitate a yellow gum (ca. 9 g) which was separated on a short path silica (7736H; 300 g) column eluted with ethyl acetate/2% isopropanol/20% triethylamine to give three products. TLC SiO2 (EtOAc/20% i-PrOH/2% Et3N) Rf 0.26, 0.39 and 0.5 respectively.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate evaporated to small volume (ca. 30 ml)
  3. additionadded to vigorously stirred light petroleum (b.p. 60°-80°: 500 ml)
  4. customto precipitate a yellow gum (ca. 9 g) which
  5. customwas separated on a short path silica (7736H; 300 g) column
  6. washeluted with ethyl acetate/2% isopropanol/20% triethylamine
  7. customto give three products

Sources & evidence

ORD record
ord-10f7471fb6bb4493aefe0db58474d20e
Source dataset
uspto-grants-1982_02
Patent number
US04316907

Reaction notes

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