Potassium Carbonate → 6-(5-Phenyl-1,3,4-oxadiazol-2-yl)methoxy-2-piperidinomethyltetralin hydrochloride

HRID 382981

反応式

HRID 382981 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2.[Cl:19][CH2:20][C:21]1[O:22][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:24][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[ClH:19].[C:26]1([C:23]2[O:22][C:21]([CH2:20][O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH2:8][CH:7]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:6][CH2:5]4)=[N:25][N:24]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 219398616-Hydroxy-2-piperidinomethyltetralin

生成物 1

HCID 229985536-(5-Phenyl-1,3,4-oxadiazol-2-yl)methoxy-2-piperidinomethyltetralin hydrochloride収率 69.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-hydroxy-2-piperidinomethyltetralin (141 mg, free form of Reference Example 19) and 2-chloromethyl-5-phenyl-1,3,4-oxadiazole (148 mg) in DMF (3 ml) was added potassium carbonate (143 mg) and the reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate:methanol=10:1) and alumina column chromatography (eluent: ethyl acetate:hexane=1:4), and then converted into its hydrochloride, which was further recrystallized from methanol-diethyl ether to obtain the titled compound (175 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate:methanol=10:1) and alumina column chromatography (eluent: ethyl acetate:hexane=1:4)
  6. customwas further recrystallized from methanol-diethyl ether

出典と根拠

ORDレコード
ord-ce53b8eaa9ab4dfe8a27a4ed5c5660c3
出典データセット
uspto-grants-2001_10
特許番号
US06310107B1

関連ノート

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