Sodium Iodide → HCID 9952163, compound

HRID 1057603Notes

Reaction equation

HRID 1057603 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:21])[C:15]=2[C:14]2[C:9]1=[C:10]([CH3:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Cl)[CH3:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:25][CH2:24][N:26]([CH2:30][CH3:31])[CH2:27][CH3:28])[C:15]=2[C:14]2[C:9]1=[C:10]([CH3:22])[CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 12967331HCID 12967331, compound

Product 1

HCID 9952163HCID 9952163, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Benzyl-8-methyl-9H-carbazol-4-ol (0.0566 g, 0.20 mmol), 2-diethylaminoethylchloride hydrochloride (0.0505 g, 0.29 mmol), potassium carbonate (0.0922 g, 0.67 mmol), sodium iodide (0.0029 g, 0.019 mmol) and DMF (1 mL) are heated at 85° C. for 4 h. After the mixture had cooled, it is partitioned between water and ether. The combined organic layers are dried over magnesium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (15 mL) using methanol/dichloromethane (1/99 to 2/98 to 4/96) to give 0.0248 g (32%) of the title compound; MS (ESI+) for C26H30N2O m/z 387.2 (M+H)+; IR (drift) 2966, 1585, 1497, 1449, 1353, 1336, 1268, 1251, 1140, 1106, 1069, 791, 743, 725, 715 cm−1; 1H NMR (CDCl3) δ1.18, 2.64, 2.81, 3.20, 4.41, 5.77, 6.69, 6.91, 6.99, 7.13, 7.22-7.33, 8.28. Anal. Calcd for C26H30N2O: C, 80.79; H, 7.82; N, 7.25. Found: C, 79.00; H, 7.76; N, 7.10.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ether
  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 (15 mL)

Sources & evidence

ORD record
ord-f4f2dffb0577476f9b0c0a0a8cabffab
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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