4-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate → HCID 20568896, compound

HRID 1578116Notes

Reaction equation

HRID 1578116 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.[N+:19]([C:22]1[CH:23]=[C:24]2[C:29](=O)[O:28][C:26](=[O:27])[C:25]2=[CH:31][CH:32]=1)([O-:21])=[O:20]>C(#N)C>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([N:1]3[C:29](=[O:28])[C:24]4[C:25](=[CH:31][CH:32]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=4)[C:26]3=[O:27])[CH2:3][CH2:4]2)=[CH:11]1

Participants

4

Reactant 2

HCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrateHCID 2309764-Nitrophthalic acid anhydride

Product 1

HCID 20568896HCID 20568896, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Amino-1-[2-(indol-3-yl)ethyl]piperidine (1.22 g, 5 mmol) was dissolved in refluxing acetonitrile (20 cm3) and a solution of 4-nitrophthalic anhydride (0.96 g, 5 mmol) in acetonitrile (10 cm3) was added dropwise with stirring to precipitate a yellow gum. The mixture was refluxed for a further 2-3 minutes then cooled in ice. The precipitated material was collected and heated in acetic anhydride on a steam bath for 1/2 hour. The solvent was evaporated. Methanol was added to the residue and evaporated to destroy excess acetic anhydride. The residue was then dissolved in very dilute aqueous acetic acid and insoluble material filtered off. The filtrate was basified by addition of conc. ammonia to precipitate a gum, which was triturated with methanol under reflux to give the title compound as a bright orange solid (0.44 g, 21%).

Workup

  1. customto precipitate a yellow gum
  2. temperatureThe mixture was refluxed for a further 2-3 minutes
  3. temperaturethen cooled in ice
  4. customThe precipitated material was collected
  5. temperatureheated in acetic anhydride on a steam bath for 1/2 hour
  6. customThe solvent was evaporated
  7. additionMethanol was added to the residue
  8. customevaporated
  9. customto destroy excess acetic anhydride
  10. dissolutionThe residue was then dissolved in very dilute aqueous acetic acid and insoluble material
  11. filtrationfiltered off
  12. additionThe filtrate was basified by addition of conc. ammonia
  13. customto precipitate a gum, which
  14. customwas triturated with methanol
  15. temperatureunder reflux

Sources & evidence

ORD record
ord-e7769b8fc27e43bdb5bc3d83a57ee965
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

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