Bromide ion → HCID 73454614, compound

HRID 1110710Notes

Reaction equation

HRID 1110710 reaction equation
[Br-].[ClH:2].[CH3:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10]/[C:11](/[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[N:12]\[OH:13])[CH2:6][CH2:5]1.Cl.CN1CCN(C/C(/C2C=CC(OCC3C=CC=CC=3)=CC=2)=N/O)CC1>>[ClH:2].[CH3:3][N:4]1[CH2:5][CH2:6][N:7]([CH2:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=2)=[N:12][OH:13])[CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 18639661HCID 18639661, compoundHCID 22154134HCID 22154134, compound

Product 1

HCID 73454614HCID 73454614, compound

Procedure

After dissolving 4.0 g of 4-benzyloxyacetophenone into 20 ml of 1,4-dioxane and 20 ml of tetrahydrofuran, 0.1 g of anhydrous aluminum chloride and 3.1 g of bromine were added under ice cooling and stirring. Further, after stirring for 5 hours under ice cooling, the reaction solution was concentrated to solid. Water and chloroform were added to the residue to separate liquid layers. Then, the chloroform layer was dried over anhydrous sodium sulfate and then concentrated to solid followed by purification by silica gel column chromatography using benzene/n-hexane (1:1) as an elute, to obtain 4.1 g of 2-bromo-1-(4-benzyloxy-phenyl)-ethanone. Then, using 3.0 g of the thus obtained bromide, 2.2 g of (Z)-2-(4-methyl-piperazin-1-yl)-1-(4-benzyloxy-phenyl)-ethanone oxime hydrochloride with the melting point of from 208° to 210° C. (decomposition) and 0.7 g of (E)-2-(4-methyl-piperazin-1-yl)-1-(4-benzyloxy-phenyl)-ethanone oxime hydrochloride with the melting point of from 210° to 212° C. were obtained in the same manner as in Example 1.

Workup

  1. customof from 210° to 212° C.
  2. customwere obtained in the same manner as in Example 1

Sources & evidence

ORD record
ord-c7e95f36224c4f408d81da459be65fa4
Source dataset
uspto-grants-1990_12
Patent number
US04977151

Reaction notes

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