1-(2-Methoxyphenyl)piperazine → 3-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-ol

HRID 2294122Notes

Reaction equation

HRID 2294122 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][CH2:4][OH:5])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 4109013-(4-(2-Methoxyphenyl)piperazin-1-yl)propan-1-olYield 89.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-bromopropanol (10.5 mL, 116 mmol), 1-(2-methoxyphenyl)piperazine (21 g, 109.23 mmol), sodium iodide (16.4 g, 109 mmol), potassium carbonate (38 g, 275 mmol) in 300 mL of acetonitrile was heated at reflux for 3 hours. The mixture was cooled and filtered. The filtrate was washed with saturated sodium chloride, dried (MgSO4) and concentrated. The residue was purified by column chromatography eluting with 5% methanol/methylene chloride. Product fractions were combined and concentrated to give 3-[4-(2-methoxyphenyl)piperazin-1-yl]-1-propanol (24.5 g, 97.86 mmol), m.p. 88°-89° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washThe filtrate was washed with saturated sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography
  9. washeluting with 5% methanol/methylene chloride
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b2d05fdc6d914e8db0935083c8eaf00f
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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