Potassium Hydroxide → HCID 67460742, compound

HRID 1815525Notes

Reaction equation

HRID 1815525 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]([O:19]C)=[O:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+]>C(O)C>[OH2:2].[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH:16]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:17]([OH:19])=[O:18])[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22499393HCID 22499393, compound

Product 1

HCID 67460742HCID 67460742, compoundYield 127.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (1) (0.026 mole) and KOH (0.13 mole) in ethanol (150 ml) was stirred at room temperature for 18 hours, heated at 50° C. for 2.5 hours and cooled to room temperature. The precipitate was filtered off, stirred in 2-propanol, filtered off, washed three times with 2-propanol and dried. This fraction was stirred and refluxed in 2-propanol. HCl/2-propanol 6N (19.94 ml) was added. The mixture was stirred and refluxed, filtered warm and stirred in water (350 ml). The precipitate was filtered off and dried, yielding 5.94 g of (±)-4-(4-nitrophenyl)-α-phenyl-1-piperazineacetic acid monohydrate (intermediate 2).

Workup

  1. temperatureheated at 50° C. for 2.5 hours
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was filtered off
  4. stirringstirred in 2-propanol
  5. filtrationfiltered off
  6. washwashed three times with 2-propanol
  7. customdried
  8. stirringThis fraction was stirred
  9. temperaturerefluxed in 2-propanol. HCl/2-propanol 6N (19.94 ml)
  10. additionwas added
  11. stirringThe mixture was stirred
  12. temperaturerefluxed
  13. filtrationfiltered
  14. temperaturewarm
  15. stirringstirred in water (350 ml)
  16. filtrationThe precipitate was filtered off
  17. customdried

Sources & evidence

ORD record
ord-89e33860b7524a2092a5ffa3f20737d1
Source dataset
uspto-grants-2005_04
Patent number
US06878724B2

Reaction notes

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