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Butylamine → (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-(3-(3-thienyl)benzyloxy]benzylamine hydrochloride
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Butylamine | HCID 8007 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| 反応物 | (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamine | HCID 19917481 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-(3-(3-thienyl)benzyloxy]benzylamine hydrochloride | HCID 19917490 | 85% |
反応手順
To 2.7 ml of tetrahydrofuran were added 360 mg (0.90 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-[3-(3-thienyl)benzyloxy]benzylamine, 8.6 mg (0.045 mmol) of copper (I) iodide, 4.1 mg (0.018 mmol) of palladium acetate and 9.5 mg (0.036 mmol) of triphenylphosphine, and further, 0.18 ml (1.8 mmol) of n-butylamine and 0.135 ml (1. 08 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 24 hours at room temperature, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 340 mg (yield: 85%) of the above identified compound as an oily free amine.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05296612 |
| 出典データセット | uspto-grants-1994_03 |
| ORD ID | ord-7bc3168c7eac492bb959fa072357d251 |
| 出典メモ | uspto-grants-1994_03 |