2,5-Dimethoxytetrahydrofuran → HCID 54342491, compound

HRID 342551Notes

Reaction equation

HRID 342551 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH:14]=[O:15])[CH2:10][CH2:9]1.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]2[CH2:9][CH2:10][N:11]([CH:14]=[O:15])[CH2:12][CH2:13]2)[CH:18]=[CH:22][CH:21]=[CH:20]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 53810755HCID 53810755, compound

Product 1

HCID 54342491HCID 54342491, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-(2-aminophenyl)piperazine-1-carbaldehyde (1.27 g, 6.2 mmol), 2,5-dimethoxytetrahydrofuran (1.13 g, 8.6 mmol) and concentrated acetic acid (4 mL) was heated 1.75 hours at reflux. The reaction mixture then was cooled in an ice-bath, diluted with water/ice and extracted with methylene chloride. The methylene chloride extract was washed with aqueous sodium hydroxide and then water, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (97.5/2.5) to give 4-(2-pyrrol-1-ylphenyl)piperazine-1-carbaldehyde (1.12 g, 4.4 mmol) as an oil.

Workup

  1. temperaturewas heated 1.75 hours
  2. temperatureat reflux
  3. temperatureThe reaction mixture then was cooled in an ice-bath
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. washwas washed with aqueous sodium hydroxide
  7. dry with materialwater, dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography on silica gel eluting with methylene chloride/methanol (97.5/2.5)

Sources & evidence

ORD record
ord-5bf102c66a2947958b16409e6425b4f8
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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