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Benzaldehyde → N-(1H-benzimidazol-2-ylmethyl)-N-[[4-[(benzylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzaldehyde | HCID 240 | — |
| 反応物 | Sodium borohydride | HCID 4311764 | — |
| 反応物 | N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine | HCID 21985008 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | N-(1H-benzimidazol-2-ylmethyl)-N-[[4-[(benzylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine | HCID 22018607 | 26% |
反応手順
Benzaldehyde (0.5 mL, 4.92 mmol) was condensed with N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (170 mg, 0.428 mmol) in dry MeOH (3 mL) for 17 h at room temperature and the resultant imine was reduced with sodium borohydride (329 mg, 8.70 mmol) for 1 h (see General Procedures A and B). Purification of the crude product by flash chromatography (14 g silica, 30:1:1 EtOAc/CH3OH/NH4OH) followed by radial chromatography (2 mm TLC plate, 100:1:1 CH2Cl2/CH3OH/NH4OH) gave the N-alkylated product (54 mg, 26%) as a foam.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07084155B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-3b54507cbfb14b84b0322c01958b4f77 |
| 出典メモ | uspto-grants-2006_08 |