Sodium Hydroxide → HCID 49842220, compound

HRID 342552Notes

Reaction equation

HRID 342552 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:12]2[CH2:17][CH2:16][N:15](C=O)[CH2:14][CH2:13]2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[OH-].[Na+]>CO>[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54342491HCID 54342491, compound

Product 1

HCID 49842220HCID 49842220, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(2-pyrrol-1-ylphenyl)piperazine-1-carbaldehyde (1.12 g, 4.4 mmol), sodium hydroxide (440 mg, 11 mmoL) and methanol (10 mL) was heated 14 hours at 50° C. The reaction mixture was allowed to cool to approximately 25° C. and then partitioned between water (20 mL) and dichloroethane (30 mL). The aqueous layer was separated and extracted with dichloroethane (3×30 mL). The combined dichloroethane was washed with brine and dried (K2CO3). The residue was purified by column chromatography on silica gel eluting with a gradient of 1 to 5% methanol/0.1% triethylamine/dichloroethane to give 1-(2-pyrrol-1-ylphenyl)piperazine (0.77 g, 3.4 mmol).

Workup

  1. temperatureto cool to approximately 25° C.
  2. custompartitioned between water (20 mL) and dichloroethane (30 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloroethane (3×30 mL)
  5. washThe combined dichloroethane was washed with brine
  6. dry with materialdried (K2CO3)
  7. customThe residue was purified by column chromatography on silica gel eluting with a gradient of 1 to 5% methanol/0.1% triethylamine/dichloroethane

Sources & evidence

ORD record
ord-644d22adfe0f4779b18dbca312fbf7ff
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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