HCID 19883681, compound → HCID 19883729, compound

HRID 846713Notes

Reaction equation

HRID 846713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1>C(O)C.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 19883681HCID 19883681, compound

Product 1

HCID 19883729HCID 19883729, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3 g of (E)-3-(4-chlorophenyl)-4'-[3-(dimethylamino)propyl]acrylophenone were dissolved in 100 ml of ethanol and, after the addition of 300 mg of 5 percent palladium on carbon, hydrogenated. After the uptake of the theoretical amount of hydrogen the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in ethanol and converted using 10M ethanolic hydrochloric acid solution into the hydrochloride which was precipitated by the addition of hexane. After recrystallization from ethyl acetate/ethanol 5:1 there were obtained 1.44 g (43%) of 3-(4-chlorophenyl)-4'-[3-(dimethylamino)propyl]propiophenone hydrochloride; m.p. 161°-164°.

Workup

  1. filtrationAfter the uptake of the theoretical amount of hydrogen the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethanol
  4. customwas precipitated by the addition of hexane
  5. customAfter recrystallization from ethyl acetate/ethanol 5:1 there

Sources & evidence

ORD record
ord-5a10bc45f2d94fd3b37ea13a5c0440cb
Source dataset
uspto-grants-1992_08
Patent number
US05137920

Reaction notes

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