Water → 1-(1,3-Benzodioxol-5-yl)-3-(4-phenylpiperazino)-1-propanone

HRID 1788670Notes

Reaction equation

HRID 1788670 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]2[O:10][CH2:11][O:12][C:8]=2[CH:7]=1)=[O:5].[C:15]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>CN(C=O)C>[C:15]1([N:21]2[CH2:26][CH2:25][N:24]([CH2:2][CH2:3][C:4]([C:6]3[CH:14]=[CH:13][C:9]4[O:10][CH2:11][O:12][C:8]=4[CH:7]=3)=[O:5])[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 2705941-(1,3-benzodioxol-5-yl)-3-chloropropan-1-one

Product 1

HCID 6762451-(1,3-Benzodioxol-5-yl)-3-(4-phenylpiperazino)-1-propanoneYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-Chloropropionyl)-1,3-benzodioxole (3 g) and N-phenylpiperazine (2.4 g) were dissolved in DMF (20 ml), triethylamine (1.7 g) was then added and the mixture was stirred for 10 hours at room temperature. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was crystallized from methanol and the resulting crystals were recrystallized from ethanol to give 5-[3-(4-phenyl-1-piperazinyl)propionyl]-1,3-benzodioxole (4.0 g, 84% yield). The characteristics of this compound are shown in Table 3 as Compound 47.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was crystallized from methanol
  6. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-117875f1ff4345cb90ccb856fbe3a579
Source dataset
uspto-grants-1987_08
Patent number
US04684651

Reaction notes

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