Water → 2-[(5-Methyl-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]-ethanamine
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]=5O)=[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:24](=[O:27])([O-])[O-].[K+].[K+].Br[CH2:31]CCCCl.O.[CH3:37][N:38](C=O)C>>[CH3:31][C:12]1[CH:13]=[C:14]2[C:22]3=[C:10]([O:9][CH2:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:21]3[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:27][CH2:24][CH2:37][NH2:38])[C:15]2=3)[CH:11]=1Participants
6
Conditions
- Temperature
- 85 °C
Procedure
To a mixture of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol (0.5 g, 1.66 mmol) in dry DMF (5 mL) is added potassium carbonate (1.15 g, 8.3 mmol) and 1-bromo-4-chlorobutane (1.4 g, 8.3 mmol). The mixture is heated at 85° C., under argon, for 4 h. The mixture is then cooled to room temperature and water (50 mL) is added. The mixture is transferred to a separatory funnel and partitioned between water and ether. The ether layer is washed with water (50 mL) then dried over anhydrous sodium sulfate. The ether filtrates are then concentrated. Column chromatography (50 mL silica) using hexanes followed by hexanes/methylene chloride (1:1) gave 0.373 g (57%) of the title compound.
Workup
- temperatureThe mixture is then cooled to room temperature
- customThe mixture is transferred to a separatory funnel
- custompartitioned between water and ether
- washThe ether layer is washed with water (50 mL)
- dry with materialthen dried over anhydrous sodium sulfate
- concentrationThe ether filtrates are then concentrated
Sources & evidence
- ORD record
- ord-64441915cf884b47bd886374dbb76e11
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06821970B2
Reaction notes
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