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 1279697

Reaction equation

HRID 1279697 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+]>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

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium Carbonate2×HCID 133631-Chloro-2-(diethylamine)ethane hydrochloride3×HCID 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 diethylaminoethyl 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-0b99c9eebf774d6482411c3e88c28fd9
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Linked notes

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