4-Chlorophthalic anhydride → HCID 20568899, compound

HRID 1578114Notes

Reaction equation

HRID 1578114 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:4][CH2:3]1.[Cl:19][C:20]1[CH:21]=[C:22]2[C:27](=O)[O:26][C:24](=[O:25])[C:23]2=[CH:29][CH:30]=1>CC#N>[Cl:19][C:20]1[CH:21]=[C:22]2[C:23](=[CH:29][CH:30]=1)[C:24](=[O:25])[N:1]([CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:4][CH2:3]1)[C:27]2=[O:26]

Participants

4

Reactant 2

HCID 670444-Chlorophthalic anhydrideHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 20568899HCID 20568899, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Amino-1-[2-(indol-3-yl)ethyl]piperidine (3.86 g, 15.9 mmol) was dissolved in warm methyl cyanide (50 cm3) and a solution of 4-chlorophthalic anhydride (2.9 g, 15.9 mmol) in methyl cyanide (20 cm3) was added dropwise with stirring, to precipitate a solid. The suspension was stirred at room temperature overnight then cooled briefly in ice and the solid collected. This crude material was heated in acetic anhydride (70 cm3) for 21/2 hours then the solvent was evaporated. The residue was dissolved in methanol, to destroy excess acetic anhydride, then the methanol was evaporated. The residue was dissolved in very dilute aqueous acetic acid and the solution was basified by addition of conc. ammonia to precipitate a gum. The supernatant layer was decanted and the gum triturated with boiling ethanol and cooled in ice to give crystals of the title compound (2.82 g, 43.6%), m.p. 188°-190° C.

Workup

  1. customto precipitate a solid
  2. stirringThe suspension was stirred at room temperature overnight
  3. temperaturethen cooled briefly in ice
  4. customthe solid collected
  5. temperatureThis crude material was heated in acetic anhydride (70 cm3) for 21/2 hours
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in methanol
  8. customto destroy excess acetic anhydride
  9. customthe methanol was evaporated
  10. dissolutionThe residue was dissolved in very dilute aqueous acetic acid
  11. additionthe solution was basified by addition of conc. ammonia
  12. customto precipitate a gum
  13. customThe supernatant layer was decanted
  14. customthe gum triturated with boiling ethanol
  15. temperaturecooled in ice

Sources & evidence

ORD record
ord-00e285bad3a541aa98cfdc4ff5c4c70b
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

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