Dicyclohexylamine → HCID 13055364, compound

HRID 1262912Notes

Reaction equation

HRID 1262912 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[CH:13]1([NH:19]C2CCCCC2)[CH2:18]CCC[CH2:14]1.S(=O)(=O)(O)[O-:27].[K+].NN>CO>[NH2:19][C@@H:13]([CH3:18])[C:14]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([OH:12])=[O:11])=[O:27]

Participants

6

Reactant 4

HCID 7582DicyclohexylamineHCID 9321HydrazineHCID 72899Indole-2-carboxylic acidHCID 516920Potassium bisulfate

Product 1

HCID 13055364HCID 13055364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(S)-2,3-Dihydro-1-[(S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindo]-2-yl)-1-oxopropyl]-1H-indole-2-carboxylic acid, dicyclohexylamine (20.4 g.) was treated with 5% aqueous potassium bisulfate solution (300 ml.), and the free acid that formed was extracted three times with methylene chloride (combined extracts 450 ml.). The combined extracts were washed with saline twice, then dried over anhydrous sodium sulfate. Evaporation of the methylene chloride on a rotary evaporator under reduced pressure, then in high vacuum gave an amorphous solid which was dissolved in methanol (200 ml.). Hydrazine (95%, 1.43 g.) was added to the methanol solution. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 24 hr., then chilled in an ice-salt mixture for 3 hr. A precipitate (phthalhydrazide, 4.06 g.) was collected on a filter, and washed with methanol. The combined filtrate and washings were evaporated on a rotary evaporator under reduced pressure, then in vacuo to give a solid residue. The residue was triturated with methylene chloride (ca. 250 ml.) and filtered. The filter residue was washed with methylene chloride several times and dried in vacuo. The crude product was dissolved in water (ca. 50 ml.) at room temperature, and filtered. The filter residue was washed with water. The combined filtrate and washings were evaporated carefully on a rotary evaporator under reduced pressure to give a solid residue which was dried over phosphorous pentoxide in vacuo to give the title product (6.31 g.), [α]D25 =-140.85 (c=1.44%, water). The analytical sample which was obtained by recrystallizations from methanol melted at 171°-172° (when the melting point was determined with rapid heating, the compound melted at 206.5°-209°), [α]D25 =-161.17° (c=1.065%, EtOH).

Workup

  1. customthe free acid that formed
  2. extractionwas extracted three times with methylene chloride (combined extracts 450 ml.)
  3. washThe combined extracts were washed with saline twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the methylene chloride
  6. customon a rotary evaporator under reduced pressure
  7. customin high vacuum gave an amorphous solid which
  8. customA precipitate (phthalhydrazide, 4.06 g.) was collected on a filter
  9. washwashed with methanol
  10. customThe combined filtrate and washings were evaporated on a rotary evaporator under reduced pressure
  11. customin vacuo to give a solid residue
  12. customThe residue was triturated with methylene chloride (ca. 250 ml.)
  13. filtrationfiltered
  14. washThe filter residue was washed with methylene chloride several times
  15. customdried in vacuo
  16. dissolutionThe crude product was dissolved in water (ca. 50 ml.) at room temperature
  17. filtrationfiltered
  18. washThe filter residue was washed with water
  19. customThe combined filtrate and washings were evaporated carefully on a rotary evaporator under reduced pressure
  20. customto give a solid residue which
  21. dry with materialwas dried over phosphorous pentoxide in vacuo

Sources & evidence

ORD record
ord-b88caa9cd9f14d4a96f08d60f7a55eb5
Source dataset
uspto-grants-1984_06
Patent number
US04454292

Reaction notes

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