Acetic Acid → HCID 14852224, compound

HRID 2107025Notes

Reaction equation

HRID 2107025 reaction equation
[Mg].[C:2]1([CH2:8][CH2:9][C:10]2[CH:11]=[C:12](Br)[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](O)(=[O:19])[CH3:18]>O1CCCC1>[C:2]1([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5462224MagnesiumHCID 14852223HCID 14852223, compound

Product 1

HCID 14852224HCID 14852224, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard compound synthesized from 1.0 g of magnesium and 10.0 g of 3-(2-phenylethyl)-bromobenzene in 30 ml of tetrahydrofuran was dropped at -60° C. under stirring for 3 min into 7.6 g of anhydrous acetic acid dissolved in 20 ml of tetrahydrofuran in a nitrogen atmosphere and stirred for further one hour. Then, the reaction solution was poured into a mixture of ice and an aqueous saturated solution of ammonium chloride and extracted with toluene. After separating the solution, it was washed with an aqueous 2N-solution of sodium hydroxide and saturated saline solution successively, dried over anhydrous sodium sulfate and then concentrated to solid. The residue was purified by silica gel column chromatography, using benzene/n-hexane (1:1) as an elute, to obtain 7.9 g of 1-(3-(2-phenylethyl)-phenyl)ethanone as an oily product. Then, by using 5.0 g of the thus obtained acetophenone compound, 3.8 g of (Z)-2-(4-methylpiperazin-1-yl)-1-(3-(2-phenylethyl)-phenyl-ethanone oxime hydrochloride with the melting point of from 185° to 188° C. (decomposition) and 0.5 g of (E)-2-(4-methylpiperazin-1-yl)-1-(3-(2-phenylethyl)-phenyl)-ethanone oxime with the melting point from 133° to 134° C. were obtained in the same manner as in Example 33.

Workup

  1. additionwas dropped at -60° C.
  2. additionThen, the reaction solution was poured into a mixture of ice
  3. extractionan aqueous saturated solution of ammonium chloride and extracted with toluene
  4. customAfter separating the solution, it
  5. washwas washed with an aqueous 2N-solution of sodium hydroxide and saturated saline solution successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to solid
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d5d68d7c594f4edba89f5a337a82144e
Source dataset
uspto-grants-1990_06
Patent number
US04933344

Reaction notes

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