Sodium Iodide → N,N-diethyl-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine

HRID 2415811Notes

Reaction equation

HRID 2415811 reaction equation
[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:20]3=[CH:19][CH:18]=[CH:17][C:16]=5[OH:23])=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:31]([N:33]([CH2:36][CH2:37]Cl)[CH2:34][CH3:35])[CH3:32].[I-].[Na+].Cl.[Cl-]>CN(C=O)C>[CH2:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH2:35][O:23][C:16]1[C:15]2[C:14]3[C:22]4=[C:10]([O:9][CH2:8][CH:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:21]4[C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH:11]=[CH:12][CH:13]=3)[CH3:32]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 133631-Chloro-2-(diethylamine)ethane hydrochloride2×HCID 6410751Hydrogen chloride dimerHCID 121486261-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol

Product 1

HCID 9930864N,N-diethyl-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamineYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol (0.048 g, 0.159 mmol), potassium carbonate (0.044 g, 0.318 mmol), and DMF (1.0 mL) at 100° C. is added diethylaminoethyl chloride hydrochloride (0.033 g, 0.191 mmol) in aliquots over 1 h. After 5.5 h, an additional 0.011 g of diethylaminoethyl chloride hydrochloride is added, and one hour later, a few crystals of sodium iodide are added. After heating for ten hours, the mixture is allowed to stir at room temperature for the remainder of the night. Additional potassium carbonate (0.022 g) and diethylarminoethyl chloride hydrochloride (0.017 g) are added and the mixture is stirred at 100° C. for 1.5 h. The major portion of the DMF is distilled off and the residue is partitioned between dichloromethane and water. The organic layers are dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel (17 mL) using EtOAc/dichloromethane (30/70 to 60/40) to give 0.040 g of N,N-diethyl-2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-1-ethanamine.

Workup

  1. temperatureAfter heating for ten hours
  2. stirringthe mixture is stirred at 100° C. for 1.5 h
  3. distillationThe major portion of the DMF is distilled off
  4. customthe residue is partitioned between dichloromethane and water
  5. dry with materialThe organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (17 mL)

Sources & evidence

ORD record
ord-d0835ad7d8234c9ba92f4ad95bc41185
Source dataset
uspto-grants-2004_11
Patent number
US06821970B2

Reaction notes

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