4-Methylphthalic anhydride → HCID 20568895, compound

HRID 1578115Notes

Reaction equation

HRID 1578115 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.[CH3:19][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>[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:27](=[O:26])[C:22]4[C:23](=[CH:29][CH:30]=[C:20]([CH3:19])[CH:21]=4)[C:24]3=[O:25])[CH2:3][CH2:4]2)=[CH:11]1

Participants

4

Reactant 2

HCID 880694-Methylphthalic anhydrideHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 20568895HCID 20568895, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Amino-1-[2-(indol-3-yl)ethyl]piperidine (1.22 g, 5 mmol) was dissolved in warm methyl cyanide (50 cm3) and a solution of 4-methylphthalic anhydride (0.81 g, 5 mmol) in methyl cyanide (10 cm3) was added dropwise with stirring to precipitate a white solid. The suspension was stirred overnight then the solid collected and heated in acetic anhydride (40 cm3) for 2 hours on a steam bath. The acetic anhydride was evaporated. The residue was dissolved in very dilute aqueous acetic acid and the solution basified by addition of conc. ammonia to give a gum. The mother liquor was decanted and the gum recrystallised from ethanol to give crystals of the title compound (0.53 g, 27.3%).

Workup

  1. customto precipitate a white solid
  2. stirringThe suspension was stirred overnight
  3. customthe solid collected
  4. temperatureheated in acetic anhydride (40 cm3) for 2 hours on a steam bath
  5. customThe acetic anhydride was evaporated
  6. dissolutionThe residue was dissolved in very dilute aqueous acetic acid
  7. additionthe solution basified by addition of conc. ammonia
  8. customto give a gum
  9. customThe mother liquor was decanted
  10. customthe gum recrystallised from ethanol

Sources & evidence

ORD record
ord-f8df08ae415f402c8befbec7afd943a5
Source dataset
uspto-grants-1981_09
Patent number
US04291042

Reaction notes

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