1-(2-Methoxyphenyl)piperazine → 1-(4-(2-Methoxyphenyl)piperazinyl)-3-(2-naphthyloxyl)propan-2-ol

HRID 918958Notes

Reaction equation

HRID 918958 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:15][CH:13]([OH:14])[CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 929952-Naphthyl glycidyl ether

Product 1

HCID 44720481-(4-(2-Methoxyphenyl)piperazinyl)-3-(2-naphthyloxyl)propan-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-((2-naphthyloxy)methyl)oxirane (75 mg, 0.38 mmol) in ethanol (0.75 mL) was added 4-(2-methoxyphenyl)piperazine (79 uL, 0.45 mmol) at room temperature. The mixture was stirred under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give HUHS1005 (149 mg, 100%).

Workup

  1. temperatureunder reflux for 1 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd764fe727ef4ce9bba66f0f46c42fe9
Source dataset
uspto-grants-2016_03
Patent number
US09272980B2

Reaction notes

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