Water → 2-(4-Benzyl-1-piperazinyl)-1-(3,4-dimethoxyphenyl)-1-ethanone

HRID 2417620Notes

Reaction equation

HRID 2417620 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].O.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:11].[CH2:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([N:29]1[CH2:34][CH2:33][N:32]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[O:11])[CH2:31][CH2:30]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 759941-BenzylpiperazineHCID 2704232-Bromo-1-(3,4-dimethoxyphenyl)ethan-1-one

Product 1

HCID 204473182-(4-Benzyl-1-piperazinyl)-1-(3,4-dimethoxyphenyl)-1-ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium carbonate (18.84 g) and water (41.4 ml) was added to a stirring suspension at 0° to 5° C. of 2-bromo-1-(3,4-dimethoxyphenyl)-1-ethanone (32.03 g, described in Example 4) and 1-benzylpiperazine (24 ml) in acetonitrile (90 ml). The suspension was stirred at room temperature for 2.5 hr and evaporated. The residue was dissolved in a mixture of water and chloroform, and the chloroform layer was dried and evaporated. Chromatographic purification on silica gel (700 g) using ethyl acetate-hexane (60:1 to 100:1) gave 32 g of 2-(4-benzyl-1-piperazinyl)-1-(3,4-dimethoxyphenyl)-1-ethanone, nmr(CDCl3) δ2.65, 3.57, 3.74, 3.89, 3.91, 6.81, 7.37 and 7.53.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in a mixture of water and chloroform
  3. dry with materialthe chloroform layer was dried
  4. customevaporated
  5. customChromatographic purification on silica gel (700 g)

Sources & evidence

ORD record
ord-9998385aff0141069165ce87b13360ae
Source dataset
uspto-grants-1984_09
Patent number
US04469695

Reaction notes

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