反応式
[Cl:1][CH2:2][CH2:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=O.[BH4-].[Na+].C(O)(=O)C.O>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2参加物
実験手順
To a solution of 3-chloro-1-(10,11-dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propanone (14.0 g, 0.044 mol) in tetrahydrofuran (150 ml) at 0° C., sodium borohydride (6.66 g, 0.176 mol) was added, followed by dropwise addition of glacial acetic acid (10.0 ml). The resulting mixture was stirred at room temperature overnight and then heated at reflux temperature for 2 h. More sodium borohydride (6.50 g, 172 mmol) and then borontrifluoride diethyl etherate (20.0 ml, 0.163 mol) were added and heating at reflux temperature was continued for h. Water (350 ml) was cautiously added and the phases were separated. The aqueous phase was extracted with toluene (3×100 ml). The combined organic phases were washed with brine (3×100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (100 g) using a gradient of heptane and ethyl acetate (10:0→10:2), to give 4.58 g (38%) of 5-(3-chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine as an oil.
後処理
- temperatureheated
- temperatureat reflux temperature for 2 h
- temperatureheating
- temperatureat reflux temperature
- customthe phases were separated
- extractionThe aqueous phase was extracted with toluene (3×100 ml)
- washThe combined organic phases were washed with brine (3×100 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel (100 g)
出典と根拠
- ORDレコード
- ord-b821050b9a2446a48dadb2ed97b22f81
- 出典データセット
- uspto-grants-2000_08
- 特許番号
- US06110913
関連ノート
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