Sodium Carbonate → 4-(4-Methylpiperazin-1-yl)benzaldehyde

HRID 2218040Notes

Reaction equation

HRID 2218040 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-fluorobenzaldehyde (10 gm, 0.08 moles) and N-methylpiperazine (14 gm, 0.14 moles) in water (80 mL) containing sodium carbonate (12.7 gm, 0.12 moles) was stirred and refluxed for 21 hours. After cooling, the mixture was poured into a separatory funnel containing water (200 mL) and the oily product was extracted into methylene chloride (3×50 mL). The combined extracts were washed with water and were then stripped under vacuum. The product, which was isolated as an oil, solidified into a tan solid upon cooling. The solid product was triturated in hexane and isolated by filtration. After drying, there was obtained 14.9 gm (91%) of N-(4-formylphenyl)-N′-methylpiperazine as an off white solid.

Workup

  1. temperaturerefluxed for 21 hours
  2. temperatureAfter cooling
  3. additionthe mixture was poured into a separatory funnel
  4. extractionthe oily product was extracted into methylene chloride (3×50 mL)
  5. washThe combined extracts were washed with water
  6. customThe product, which was isolated as an oil
  7. temperatureupon cooling
  8. customThe solid product was triturated in hexane
  9. customisolated by filtration
  10. customAfter drying

Sources & evidence

ORD record
ord-0821d25402dc477099c717d57a5319ba
Source dataset
uspto-grants-2008_08
Patent number
US07410975B2

Reaction notes

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