1-(2-Methoxyphenyl)piperazine → HCID 9291364, compound

HRID 1645820Notes

Reaction equation

HRID 1645820 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH2:15]1[O:23][C@@H:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1OC1C1C=CC=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:23])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 7276Styrene OxideHCID 114705(+)-Styrene oxide

Product 1

HCID 9291364HCID 9291364, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methoxyphenylpiperazine (19.84 g, 0.103 m) in dry acetonitrile (150 ml) was refluxed with (R)-styrene oxide (12.4 g, 0.104 m). The residue on evaporation was chromatographed on silica using ethyl acetate as eluant to give two main fractions. The first fraction (4.3 g) contained some styrene oxide, which was removed by acid-base extraction to give 3.55 g of pure title compound. The second fraction (9.5 g) was 95% title compound and approximately 5% of the regioisomer.

Workup

  1. customThe residue on evaporation
  2. customwas chromatographed on silica
  3. customto give two main fractions
  4. customwas removed by acid-base extraction

Sources & evidence

ORD record
ord-033d4c4fe20a4c889de992273e9ef229
Source dataset
uspto-grants-1993_01
Patent number
US05177078

Reaction notes

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