Water → HCID 10389536, compound

HRID 370659Notes

Reaction equation

HRID 370659 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]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[C:32]=1[O:41][CH3:42])=[O:30].O>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]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[C:32]=3[O:41][CH3:42])=[O:30])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70048BenzhydrylpiperazineHCID 27571992-bromo-1-(2,3,4-trimethoxyphenyl)ethanone

Product 1

HCID 10389536HCID 10389536, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

In 60 ml of isopropanol were taken up 11.9 g (47 mmol) of 1-diphenylmethylpiperazine and 5.23 g (52 mmol) of triethylamine, and the resultant mixture was added with a solution which had been prepared by dissolving 13.6 g (47 mmol) of 2-bromo-1-(2,3,4-trimethoxyphenyl)ethanone in 50 ml of isopropanol. After being stirred for 3 hours at room temperature, the reaction mixture was poured into 200 ml of water. The mixture was extracted with 150 ml of ethyl acetate. The thus obtained organic layer was washed successively with water and saturated saline and thereafter dried over anhydrous sodium sulfate. After removal of the solvent, the residue was recrystallized from ethanol to give 14.8 g of 2-(4-diphenylmethylpiperazinyl)-1-(2,3,4-trimethoxyphenyl)ethanone (yield: 68%).

Workup

  1. customhad been prepared
  2. extractionThe mixture was extracted with 150 ml of ethyl acetate
  3. washThe thus obtained organic layer was washed successively with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-aa0a5fb180d544bca62edd1c193faea4
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Reaction notes

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