Dimethylformamide → 4-(6-Methoxy-2-pyridinyl)1-piperazinecarboxaldehyde

HRID 1031482Notes

Reaction equation

HRID 1031482 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.[CH3:14][O-:15].[Na+].CN([CH:20]=[O:21])C>>[CH3:14][O:15][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH:20]=[O:21])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 30244991-(6-Chloropyridin-2-yl)piperazineHCID 10942334Sodium Methoxide

Product 1

HCID 221678574-(6-Methoxy-2-pyridinyl)1-piperazinecarboxaldehydeYield 81%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(6-chloro-2-pyridinyl)piperazine (6.0 g) and NaOMe (16.42 g) in DMF (25 mL,) was heated at 100° C. under nitrogen atmosphere for 20 h. The excess DMF was then removed under reduced pressure. Water (5 mL) was added to the residue and the mixture extracted with CH2Cl2. The combined organic layers were washed with sat. NaCl solution, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure. Silica gel chromatography (CH2Cl2 /MeOH; 98:2) of the concentrate yielded the 4-(6-methoxy-2-pyridinyl)1-piperazinecarboxaldehyde (5.13 g; 81%).

Workup

  1. customThe excess DMF was then removed under reduced pressure
  2. additionWater (5 mL) was added to the residue
  3. extractionthe mixture extracted with CH2Cl2
  4. washThe combined organic layers were washed with sat. NaCl solution
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd2e45fbf00742489f8852ea847db85d
Source dataset
uspto-grants-1990_09
Patent number
US04954502

Reaction notes

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