반응 #433972
ord-26cc5f7d9a1e44df8fee5daf1b530e31
반응 방정식
반응물
시약
반응 조건
후처리
- 1농축the mixture was concentrated
- 2기타ether (10 ml), and the phases were separated
- 3추출extracted with EE (4×10 ml)
- 4세척The combined organic extracts were washed with 1M NaOH (2×3 ml)
- 5기타dried
- 6여과filtered
- 7농축concentrated
- 8기타For the preparation of the hydrochloride
- 9workup.WAITwas carried out for 1 h at RT
- 10workup.WAITAfter 1 h at 4° C.
- 11여과the resulting precipitate was filtered off with suction
- 12세척washed with cold 2-butanone (1 ml) and cold ether (2×1 ml)
- 13기타dried in vacuo
- 14기타The target compound was obtained in a yield of 168 mg (colourless solid, m.p. 163–168° C. with decomposition)
실험 절차
The non-polar diastereoisomer of (4-aminomethyl-1-phenylcyclohexyl)dimethylamine (232 mg, 1.0 mmol.) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (415 mg, 1.5 mmol.) were added to a solution of 3-(1H-indol-3-yl)propionic acid (189 mg, 1.0 mmol.) in abs. methanol, and stirring was carried out for 20 h at RT. For working up, the mixture was concentrated, the residue was taken up in water (10 ml) and ether (10 ml), and the phases were separated. The aqueous phase was adjusted to pH 11 with 5M NaOH and extracted with EE (4×10 ml). The combined organic extracts were washed with 1M NaOH (2×3 ml), dried, filtered and concentrated. For the preparation of the hydrochloride, the resulting non-polar diastereoisomer of N-(4-dimethylamino-4-phenylcyclohexylmethyl)-2-(1H-indol-3-yl)propionamide (220 mg, 0.54 mmol.) was dissolved in 2-butanone; chlorotrimethylsilane (104 μl, 0.82 mmol.) was added thereto, and stirring was carried out for 1 h at RT. After 1 h at 4° C., the resulting precipitate was filtered off with suction, washed with cold 2-butanone (1 ml) and cold ether (2×1 ml) and dried in vacuo. The target compound was obtained in a yield of 168 mg (colourless solid, m.p. 163–168° C. with decomposition).