Acetophenone → HCID 86743998, compound

HRID 1110712Notes

Reaction equation

HRID 1110712 reaction equation
C(C1C=CC=CC=1)(=O)C.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18]/[C:19](/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:23]=2)=[N:20]\[OH:21])[CH2:14][CH2:13]1.CN1CCN(C/C(/C2C=CC=C(CCC3C=CC=CC=3)C=2)=N/O)CC1>>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:23]=2)=[N:20][OH:21])[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 7410AcetophenoneHCID 14852225HCID 14852225, compoundHCID 18642310HCID 18642310, compound

Product 1

HCID 86743998HCID 86743998, compound

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. customfrom 133° to 134° C.
  2. customwere obtained in the same manner as in Example 33

Sources & evidence

ORD record
ord-92886c177dab4a319f9c74ed629e7888
Source dataset
uspto-grants-1990_12
Patent number
US04977151

Reaction notes

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