Sodium Hydroxide → 1-(6-Methoxypyridin-2-yl)piperazine

HRID 1031483Notes

Reaction equation

HRID 1031483 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12](C=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221678574-(6-Methoxy-2-pyridinyl)1-piperazinecarboxaldehyde

Product 1

HCID 122004701-(6-Methoxypyridin-2-yl)piperazineYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the formamide intermediate, prepared above, (3.55 g) in 6 N HCl (30 mL) was heated at reflux for 1/2 h. The reaction was cooled to 0° C., made basic with 10N NaOH, and extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with sat. NaCl solution, dried with anhydrous K2CO3, filtered, and concentrat.ed under reduced pressure to afford 1-(6-methoxy-2-pyridinyl)piperazine (2.72 g; 83%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1/2 h
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. washThe combined organic layers were washed with sat. NaCl solution
  5. dry with materialdried with anhydrous K2CO3
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d636a17454e748fb971a75061d951554
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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