Allylamine → HCID 22725870, compound

HRID 348225Notes

Reaction equation

HRID 348225 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=O)[C:3](=[C:4]23)[CH:2]=1)=[O:22].[CH2:26]([NH2:29])[CH:27]=[CH2:28]>CN1CCCC1=O>[CH2:26]([N:29]1[C:21](=[O:22])[C:5]2[C:4]3[C:19]4[C:8](=[CH:7][CH:6]=2)[C:9]2[C:20]5[C:13]([CH:12]=[CH:11][CH:10]=2)=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]=4[CH:1]=[CH:2][C:3]=3[C:24]1=[O:23])[CH:27]=[CH2:28]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 11759069Perylene-3,4-dicarboxylic anhydride

Product 1

HCID 22725870HCID 22725870, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5 g (15.5 mmol) of perylene-3,4-dicarboxylic anhydride (prepared in accordance with Liebigs Ann. 1995, 1229–1244), 11.4 g (0.2 mol) of allylamine and 1200 ml of N-methylpyrrolidone was heated at 85° C. in a 2 1 autoclave for 7 h and then cooled to room temperature, the autoclave was let down, the solvent was reduced to about 25% of its original volume by concentration, and the precipitation of the crude product was completed by adding four times the amount of methanol. The precipitate formed was isolated by filtration, washed with methanol and dried at 60° C. under reduced pressure. Chromatographic separation on silica gel using 40:1 chloroform/methanol as eluent, followed by twofold recrystallization from chloroform, gave 4.83 g (86%) of the desired end product in the form of brownish red crystals which underwent decomposition at temperatures above 260° C.

Workup

  1. temperaturecooled to room temperature
  2. concentrationthe solvent was reduced to about 25% of its original volume by concentration
  3. customthe precipitation of the crude product
  4. additionby adding four times the amount of methanol
  5. customThe precipitate formed
  6. customwas isolated by filtration
  7. washwashed with methanol
  8. customdried at 60° C. under reduced pressure
  9. customChromatographic separation on silica gel using 40:1 chloroform/methanol as eluent
  10. customfollowed by twofold recrystallization from chloroform
  11. customgave 4.83 g (86%) of the desired end product in the form of brownish red crystals which
  12. customat temperatures above 260° C.

Sources & evidence

ORD record
ord-d6cff82a53f34f869e4af1e955ff1975
Source dataset
uspto-grants-2007_02
Patent number
US07176255B2

Reaction notes

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