Sodium hydride → (r)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine

HRID 1859422ノート

反応式

HRID 1859422 の反応式
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[C@@H:19]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:20]1>CCCCCC.CS(C)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@@H:20]2[CH2:19][N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=3[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]2=3)=[CH:33][CH:32]=1

参加物

8

反応物 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 22975052(r)-3-Chloro-1-(4-methoxyphenethyl)homopiperidine

生成物 1

HCID 15520941(r)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

60% Sodium hydride (88 mg, 2.2 mmol) was washed with hexane under argon atmosphere, and then suspended in dimethyl sulfoxide (10 ml). The obtained suspension was stirred at room temperature for 30 minutes. 5,11-Dihydrodibenzo[b,e][1,4]oxazepine (0.40 g, 2 mmol) was added to the suspension, and they were stirred at room temperature for 30 minutes and then at 50° C. for 30 minutes. A solution of (R)-3-chloro-1-(4-methoxyphenethyl)homopiperidine (0.59 g, 2.2 mmol) in dimethyl sulfoxide (5 ml) was added dropwise into the obtained solution, and they were stirred at 50° C. for 2 hours. The reaction liquid was distributed in saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduce pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with hexane and ethyl acetate (6:1) and then with hexane and ethyl acetate (3:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (R)-5,11-dihydro-5-[1-(4-methoxyphenethyl) piperidine-2-ylmethyl] dibenzo[b,e][1,4]oxazepine in the form of a light yellow solid (0.63 g, 73%).

後処理

  1. stirringwere stirred at room temperature for 30 minutes
  2. waitat 50° C. for 30 minutes
  3. stirringwere stirred at 50° C. for 2 hours
  4. customThe reaction liquid
  5. customThe organic layer was dried
  6. customthe solvent was evaporated
  7. washThe product was eluted with hexane and ethyl acetate (6:1)
  8. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-0e069656617542a2964e01cbe50027e6
出典データセット
uspto-grants-2003_03
特許番号
US06528504B2

反応ノート

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