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Phenethylamine → N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Phenethylamine | HCID 1001 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| 反応物 | 4-Benzyloxy-1-methyl-1H-indole-2-carboxylic acid | HCID 4777678 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide | HCID 131725790 | — |
反応手順
To a solution of 4-benzyloxy-1-methyl-1H-indole-2-carboxylic acid (0.20 g) in DMF (10 mL) was added TBTU (0.23 g), HOBt (0.11 g) and DIEA (0.27 mL). After 5 min., phenethylamine (0.11 mL) was added and stirring was continued overnight under nitrogen at room temperature. The residue remaining after DMF evaporation was dissolved in EtOAc; washed with dilute HCl, saturated NaHCO3, and brine; dried over MgSO4; and concentrated at reduced pressure to give the intermediate product N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide (0.18 g) which was used without further purification. Hydrogenation of this product by a method analogous to that described in Example 9 give 0.14 g of the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07402604B2 |
| 出典データセット | uspto-grants-2008_07 |
| ORD ID | ord-d32f939899cb4a6bb5e5065127b0b33e |
| 出典メモ | uspto-grants-2008_07 |