Sodium Iodide → N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amine

HRID 1057633Notes

Reaction equation

HRID 1057633 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:23])[C:5]2=1.Cl.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29]Cl)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][O:23][C:6]1[C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([F:1])[CH:3]=3)[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH3:26]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 186716846-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol

Product 1

HCID 18671674N,N-Diethyl-N-(2-{[6-fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-yl]oxy}ethyl)amineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Fluoro-9-(4-fluorobenzyl)-9H-carbazol-4-ol (0.0584 g, 0.19 mmol), 2-diethylaminoethylchloride hydrochloride (0.0593 g, 0.35 mmol), potassium carbonate (0.0926 g, 0.63 mmol), sodium iodide (0.0061 g, 0.041 mmol) and DMF (2 mL) are heated at 85° C. for 3 h. After the mixture had cooled, it is partitioned between water and ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (50 mL) using methanol/dichloromethane (1/99) to give 0.0471 g (61%) of the title compound; mp 75-76° C.; MS (ESI+) for C25H26F2N2O m/z 409.3 (M+H)+; IR (drift) 1585, 1507, 1481, 1461, 1343, 1269, 1221, 1159, 1145, 871, 820, 799, 776, 739, 712 cm−1; 1H NMR (CDCl3) δ1.14, 2.73, 3.10, 4.33, 5.44, 6.69, 6.93, 7.04-7.18, 7.36, 8.03. Anal. Calcd for C25H26F2N2O: C, 73.51; H, 6.41; N, 6.86. Found:C, 73.30; H, 6.59; N, 6.77.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel (50 mL)

Sources & evidence

ORD record
ord-64237b9df4584a5a88f63fa44e21e0e1
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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