2-Bromo-1-(4-hydroxyphenyl)ethanone → 2-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone

HRID 370656Notes

Reaction equation

HRID 370656 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)=[O:30]>C(O)(C)C>[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:28][C:29]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)=[O:30])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 8471TriethylamineHCID 70048Benzhydrylpiperazine

Product 1

HCID 103401292-(4-Diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanoneYield 84.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

2.52 g (10 mmol) of 1-diphenylmethylpiperazine and 1.11 g (11 mmol) of triethylamine were dissolved in 30 ml of isopropanol, followed by addition of a solution obtained by dissolving 2.15 g (10 mmol) of α-bromo-p-hydroxyacetophenone in 20 ml of isopropanol. The mixture was allowed to stand overnight at room temperature. Precipitated crystals were collected by filtration. The crystals were successively washed with isopropanol, water and isopropanol and then dried to give 3.27 g of crude crystals of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone (yield: 84.6%).

Workup

  1. additionfollowed by addition of a solution
  2. customobtained
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washThe crystals were successively washed with isopropanol, water and isopropanol
  6. customdried

Sources & evidence

ORD record
ord-80beec8bb1a84b579b1dfbd3da8dfa71
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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