関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 反応物 | 4-Benzylidene-piperidine | HCID 10773559 | — |
| 反応物 | 2-[3-(1-Piperidinyl)propoxy]benzaldehyde | HCID 13795259 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 生成物 | 1-{3-[2-(4-Benzylidene-piperidin-1-ylmethyl)-phenoxy]-propyl}-piperidine | HCID 17962601 | — |
| 生成物 | Ammonia dichloromethane | HCID 22731429 | 1% |
反応手順
A solution of 2-(3-piperidin-1-yl-propoxy)-benzaldehyde (212 mg), 4-benzylidene-piperidine (154 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (6 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (148 mg). 1H NMR (400 MHz, CDCl3): 7.37 (m, 1H), 7.30 (m, 2H), 7.23-7.16 (m, 4H), 6.92 (m, 1H), 6.86 (m, 1H), 6.27 (s, 1H), 4.00 (t, J=6.3 Hz, 2H), 3.60 (s, 2H), 2.60 (m, 2H), 2.55-2.46 (m, 6H), 2.44-2.37 (m, 6H), 2.00 (m, 2H), 1.64-1.56 (m, 4H), 1.47-1.40 (m, 2H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07429586B2 |
|---|
| 出典データセット | uspto-grants-2008_09 |
|---|
| ORD ID | ord-1a50cbcded61442b986ca447337dd1f9 |
|---|
| 出典メモ | uspto-grants-2008_09 |
|---|
