3,4-Methylenedioxybenzyl-(3-azepin-1-yl-propyl)-amine → 3,4-Methylenedioxybenzyl-[3-(3,5-difluorophenyl)-isoxazol-5-yl]-(3-azepin-1-yl-propyl)-amine hydrochloride

HRID 1264531ノート

反応式

HRID 1264531 の反応式
[CH2:1]1[O:21][C:20]2[CH:19]=[CH:18][C:5]([CH2:6][NH:7][CH2:8][CH2:9][CH2:10][N:11]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][C:3]=2[O:2]1.[Li]CCCC.[F:27][C:28]1[CH:29]=[C:30]([C:35]2[CH:39]=[C:38]([Cl:40])[O:37][N:36]=2)[CH:31]=[C:32]([F:34])[CH:33]=1>C(OCC)C.CCCCCC.C(OCC)(=O)C>[ClH:40].[CH2:1]1[O:21][C:20]2[CH:19]=[CH:18][C:5]([CH2:6][N:7]([C:38]3[O:37][N:36]=[C:35]([C:30]4[CH:29]=[C:28]([F:27])[CH:33]=[C:32]([F:34])[CH:31]=4)[CH:39]=3)[CH2:8][CH2:9][CH2:10][N:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:4][C:3]=2[O:2]1

参加物

7

反応物 3

HCID 186126483,4-Methylenedioxybenzyl-(3-azepin-1-yl-propyl)-amineHCID 186126645-Chloro-3-(3,5-difluorophenyl)isoxazoleHCID 178418339Butyllithium

生成物 1

HCID 186126573,4-Methylenedioxybenzyl-[3-(3,5-difluorophenyl)-isoxazol-5-yl]-(3-azepin-1-yl-propyl)-amine hydrochloride

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3,4-methylenedioxybenzyl-(3-azepin-1-yl-propyl)amine in diethyl ether (26.7 ml of a 0.12 M solution in diethyl ether, 3.22 mmol) cooled to 0° C. is slowly added n-BuLi (1.51 ml of a 1.6M solution in hexane, 2.41 mmol). The resulting mixture is stirred at 0° C. for 10 min and 3-(3,5-difluorophenyl)-5-chloroisoxazole (347 mg, 1.61 mmol) is added at once. After stirring at 0° C. for 30 min, the reaction mixture is dilute with ethyl acetate, washed with water andbrine, dried over sodium sulfate, and concentrated in vacuo. The crude material is purified by flash chromatography (silica gel, 3% methanol containing 10% NH4OH in dichloromethane) to give the free base of the title compound as an oil. The free base is dissolved in dichloromethane (10 ml) and treated with 1 N HCl in diethyl ether (4 ml, 4 mmol) to provide after concentration in vacuo, 3,4-methylenedioxybenzyl-[3-(3,5-difluorophenyl)-isoxazol-5-yl]-(3-azepin-1-yl-propyl)-amine hydrochloride (513 mg, 63%) as a pale yellow foam.

後処理

  1. stirringAfter stirring at 0° C. for 30 min
  2. washwashed with water andbrine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by flash chromatography (silica gel, 3% methanol containing 10% NH4OH in dichloromethane)

出典と根拠

ORDレコード
ord-0f8ae4ef8613414fbf37bfc0bd0e4e30
出典データセット
uspto-grants-2003_04
特許番号
US06544982B1

反応ノート

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