Sodium Hydroxide → HCID 23454740, compound

HRID 1680816Notes

Reaction equation

HRID 1680816 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([O:7][CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)=O)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[O:7][C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 23454739HCID 23454739, compound

Product 1

HCID 23454740HCID 23454740, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 4,070 g of 1-[α-(4-methoxyphenoxy)-phenylacetyl]-4-ethoxycarbonyl piperazine, 20,000 ml of toluene and 2,850 ml of phosphorus oxychloride is stirred under nitrogen at 98° for 24 hours. It is poured hot onto 100 kg of crushed ice, followed by 10,000 ml of 50% aqueous sodium hydroxide. After stirring for 30 minutes the organic phase is separated and the aqueous layer extracted with 10,000 ml of toluene. The combined toluene solutions are washed with 10,000 ml of 2 N aqueous sodium hydroxide and 4 times with 10,000 ml of water, dried, filtered and evaporated at about 60°, to yield the 1-(5-methoxy-2-phenyl-3-benzofuryl)-4-ethoxycarbonylpiperazine showing in the NMR-spectrum peaks centered at 8.09, 3.72 and 3.12 ppm.

Workup

  1. stirringAfter stirring for 30 minutes the organic phase
  2. customis separated
  3. extractionthe aqueous layer extracted with 10,000 ml of toluene
  4. washThe combined toluene solutions are washed with 10,000 ml of 2 N aqueous sodium hydroxide and 4 times with 10,000 ml of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated at about 60°

Sources & evidence

ORD record
ord-99abddff26ff44a89e07dec6ea4b2891
Source dataset
uspto-grants-1981_06
Patent number
US04276294

Reaction notes

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