1-Piperazinecarboxaldehyde → HCID 19421679, compound

HRID 2380698Notes

Reaction equation

HRID 2380698 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:35]C(O)=O)=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C(Cl)Cl>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:34]([C:31]2[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[CH:33][CH:32]=2)=[CH:35][C:18]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 821911-PiperazinecarboxaldehydeHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 12660800HCID 12660800, compound

Product 1

HCID 19421679HCID 19421679, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3.41 ml of diphenylphosphoryl azide and 1.09 ml of 1-formylpiperazine were added to a 60 ml of a methylene chloride solution of 3.00 g of 3,3-bis(4-methoxyphenyl)acrylic acid and 2.94 ml of triethylamine. The reaction mixture was then stirred for 2 hours at room temperature, after which it was poured into a saturated aqueous solution of sodium bicarbonate and extracted twice with methylene chloride. The combined extracts were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was dissolved in 80 ml of methanol, and 40 ml of a 10% w/v aqueous solution of sodium hydroxide were added to the resulting solution. The reaction mixture was stirred for 18 hours at room temperature and then poured into water; it was then extracted twice with methylene chloride. The combined extracts were washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography through 80 g of silica gel eluted with mixtures of methylene chloride and methanol ranging from 19:1 to 4:1 by volume to give 3.00 g of 1-[3,3-bis(4-methoxyphenyl)acryloyl]piperazine as a powder.

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe combined extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 80 ml of methanol
  6. addition40 ml of a 10% w/v aqueous solution of sodium hydroxide were added to the resulting solution
  7. stirringThe reaction mixture was stirred for 18 hours at room temperature
  8. additionpoured into water
  9. extractionit was then extracted twice with methylene chloride
  10. washThe combined extracts were washed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customevaporated under reduced pressure
  13. customThe residue was purified by column chromatography through 80 g of silica gel
  14. washeluted with mixtures of methylene chloride and methanol ranging from 19:1 to 4:1 by volume

Sources & evidence

ORD record
ord-2c9f6692b0124434bd4b967e8946b25f
Source dataset
uspto-grants-1994_11
Patent number
US05369106

Reaction notes

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