1-(2-Methoxyphenyl)piperazine → HCID 9291366, compound

HRID 1645821Notes

Reaction equation

HRID 1645821 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>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

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 114946(S)-styrene oxide

Product 1

HCID 9291366HCID 9291366, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methoxyphenylpiperazine (17.4 g, 0.0906 m) in dry acetonitrile (150 ml) was refluxed 24 hrs with (S)-styrene oxide (10.84 g, 0.09 m). The residue on evaporation was treated by acid-base extraction to remove unreacted styrene oxide to leave 28 g of the crude alcohol as a mixture of regioisomers which was purified by chromatography on silica, using 1:1 hexane ethylacetate, to give 16.5 g of the pure isomer, [α]23D +56° C.

Workup

  1. customThe residue on evaporation
  2. additionwas treated by acid-base extraction
  3. customto remove unreacted styrene oxide

Sources & evidence

ORD record
ord-c82b5096421749a49b0d60eda1989a55
Source dataset
uspto-grants-1993_01
Patent number
US05177078

Reaction notes

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