Carbazole, 9-(3-(dimethylamino)propyl)- → 1,1'-{9-[3-(Dimethylamino)propyl]-9H-carbazole-3,6-diyl}bis(2-methylpropan-1-one)

HRID 514756Notes

Reaction equation

HRID 514756 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:12]1[C:11]2[CH:10]=[CH:9][C:8]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[C:3]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH:4]=2

Participants

5

Reactant 3

HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 453806051,1'-{9-[3-(Dimethylamino)propyl]-9H-carbazole-3,6-diyl}bis(2-methylpropan-1-one)Yield 48.1%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Compound 30 (0.25 g, 1.0 mmol) was dissolved in nitrobenzene (5 mL). AlCl3 (0.6 g, 4.5 mmol) and then isobutyroyl chloride (0.6 mL, 5.7 mmol) were added in portions. The reaction mixture was stirred for 40 min (LC/MS monitoring). The obtained mixture was poured into ice/water mixture and extracted with CHCl3. The combined extracts were evaporated, and the residue was purified by chromatography in a short thick silica gel column (eluent: CHCl3/MeOH 99:1→90:10) to afford 0.189 g (47%) of the product. 1H NMR (DMSO-d6): δ 1.20 (12H, d, J=6.7 Hz); 1.90-1.97 (2H, m); 2.11 (6H, s); 2.18 (2H, t, J=6.7 Hz); 3.91 (2H, septet, J=6.7 Hz), 4.50 (2H, t, J=6.6 Hz); 7.76 (2H, d, J=8.7 Hz); 8.14 (2H, dd, J=8.7 Hz, J=1.5 Hz); 9.11 (2H, d, J=1.5 Hz). ELSD: 100%, ESI-MS: m/z 392 [M+H]+.

Workup

  1. extractionextracted with CHCl3
  2. customThe combined extracts were evaporated
  3. customthe residue was purified by chromatography in a short thick silica gel column (eluent: CHCl3/MeOH 99:1→90:10)

Sources & evidence

ORD record
ord-47e1f6b8566f431faffec9146346b49d
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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