Sodium Iodide → HCID 9821567, compound

HRID 1057635Notes

Reaction equation

HRID 1057635 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=[CH:10][CH:11]=[C:12]([CH3:22])[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=[CH:10][CH:11]=[C:12]([CH3:22])[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 18671667HCID 18671667, compound

Product 1

HCID 9821567HCID 9821567, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Benzyl-6-methyl-9H-carbazol-4-ol (0.0597 g, 0.21 mmol), 2-diethylaminoethylchloride hydrochloride (0.0565 g, 0.33 mmol), potassium carbonate (0.1007 g, 0.73 mmol), sodium iodide (0.0054 g, 0.036 mmol) and DMF (1 mL) are heated at 85° C. for 4.5 h. After the mixture had cooled, it is partitioned between water and ether. The aqueous layer is also washed twice with ethyl acetate. The combined organic layers are dried over magnesium sulfate and concentrated to dryness. The residue is chromatographed on silica gel (60 mL) using methanol/dichloromethane (1/99 to 3/97 to 5/95) to give 0.0605 g (75%) of the title compound containing N-{2-[(9-benzyl-3-bromo-6-methyl-9H-carbazol-4-yl)oxy]ethyl}-N,N-diethylamine as an impurity. Attempts at purifying this material through recrystallization are unsuccessfull; MS (ESI+) for C26H30N2O m/z 387.3 (M+H)+. 1H NMR (CDCl3) δ1.17 2.53, 2.78, 3.17, 4.37, 5.47, 6.68, 6.96, 7.11, 7.21-7.34, 8.17.

Workup

  1. temperatureAfter the mixture had cooled
  2. customit is partitioned between water and ether
  3. washThe aqueous layer is also washed twice with ethyl acetate
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue is chromatographed on silica gel (60 mL)

Sources & evidence

ORD record
ord-e6ade2f7cdcc43df86395617f67e0a28
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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