1-Bromo-3-chloropropane → 3-Chloropropyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl Ether

HRID 1279724Notes

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.Br[CH2:25][CH2:26][CH2:27][Cl:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:25][CH2:26][CH2:27][Cl:28])=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol (0.82 g, 2.7 mmol) in dry DMF (12 mL) is added 1-bromo-3-chloropropane (1.28 g, 8.1 mmol) and potassium carbonate (1.12 g, 8.1 mmol). The mixture is heated at 80° C. for 6 h. The mixture is then stirred at room temperature for 18 h followed by another 6 h at 80° C. The mixture is partitioned between water and CH2Cl2. The organic layer is washed 3 times with water (100 mL). The organic layer is then dried over anhydrous sodium sulfate and concentrated. Column chromatography (60 mL silica) using hexanes/CH2C2 (1:1) as eluent gave an oil which is rechromatographed (60 mL silica) using hexanes/CH2C2 (60/40) as eluent gave 0.454 g (44%) of the title compound.

Workup

waitfollowed by another 6 h at 80° C
customThe mixture is partitioned between water and CH2Cl2
washThe organic layer is washed 3 times with water (100 mL)
dry with materialThe organic layer is then dried over anhydrous sodium sulfate
concentrationconcentrated
customgave an oil which
customis rechromatographed (60 mL silica)

Sources & evidence

ORD record: ord-78da6ae23e9143a28b01eef1263ff734
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448397B1

Reaction notes

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