Toluene → HCID 67273798, compound

HRID 599498Notes

Reaction equation

HRID 599498 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](C=O)=[CH:2]1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[C:17]1(C)C=CC=CC=1>>[N:12]1([CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[CH2:17])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 10256Indole-3-CarboxaldehydeHCID 31268Pyrrolidine

Product 1

HCID 67273798HCID 67273798, compoundYield 87%

Procedure

In a round bottom flask equipped with a Dean-Starck condenser, 1H-indole-3-carbaldehyde (40 g, 0.275 mmol) and pyrrolidine (27 ml, 0.330 mmol) were suspended in toluene (480 ml) and kept heating at reflux overnight. After cooling to rt, the solid was filtered off, washed with toluene and recrystallized from THF (100 ml) affording subtitle compound (47.7 g) as a reddish solid in 87% yield.

Workup

  1. temperaturekept heating
  2. temperatureat reflux overnight
  3. filtrationthe solid was filtered off
  4. washwashed with toluene
  5. customrecrystallized from THF (100 ml)

Sources & evidence

ORD record
ord-f0ff3d7808da4537be03b8a9bc292bfd
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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