Piperidine → 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

HRID 914692Notes

Reaction equation

HRID 914692 reaction equation
[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[CH2:15][C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2].N1CCCCC1.[NH:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([CH:50]=O)=[CH:42]1>C1(C)C=CC=CC=1>[NH:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]([CH:50]=[C:15]2[C:14]3[N:10]([C:11]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:12][N:13]=3)[C:9]3[CH:24]=[CH:25][CH:26]=[CH:27][C:8]=3[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:28])[C:16]2=[O:17])=[CH:42]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 10256Indole-3-CarboxaldehydeHCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

Product 1

HCID 1363524502-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide (Preparation 7(A)) (1.2 g, 2.7 mmol) and piperidine (0.4 mL, 1.33 mmol) in toluene was added 1H-indole-3-carbaldehyde (0.46 g, 3.2 mmol). The reaction mixture was heated at 110° C. for 31 hours. Activated 4 Å molecular sieves (2 g) were added. The reaction mixture was heated for 24 hours at 110° C. The reaction was cooled to room temperature and the molecular sieves were filtered with the aid of toluene. The filtrate was concentrated and the residue was purified by chromatography (12%-20% acetone/methylene chloride) to give 1.5 g of 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide as a solid. MS 579.2 (M+1).

Workup

  1. additionActivated 4 Å molecular sieves (2 g) were added
  2. temperatureThe reaction mixture was heated for 24 hours at 110° C
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationthe molecular sieves were filtered with the aid of toluene
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by chromatography (12%-20% acetone/methylene chloride)

Sources & evidence

ORD record
ord-3e55023cd40f43cbbee47738dc591161
Source dataset
uspto-grants-2007_09
Patent number
US07265104B2

Reaction notes

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