Diethyl Ether → 1-cyclopentyl-N-[(1R)-1-phenylethyl]ethanimine

온도

0 °C

(R)-1-Phenylethanamine (1.36 ml, 1.2 mmol) and triethylamine (7.46 ml, 53.5 mmol) were dissolved in DCM (30 ml) and cooled to 0° C. Titanium tetrachloride (0.49 ml, 4.46 mmol) was added, followed by the solution of 1-cyclopentyl-ethanone (1 g, 8.92 mmol) in DCM (5 ml). The reaction mixture was stirred 3 h at reflux temperature. After cooling to rt diethylether was added (130 ml) and the reaction mixture was filtered. The filtrate was collected and the solvents were evaporated at reduced pressure to give the product as yellow, viscous oil (2.04 g, crude quantitative). [1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]

1. temperatureat reflux temperature
2. additionwas added (130 ml)
3. filtrationthe reaction mixture was filtered
4. customThe filtrate was collected
5. customthe solvents were evaporated at reduced pressure
6. customto give the product as yellow, viscous oil (2.04 g
7. custom[1H-NMR (DMSO-d6, 600 MHz) δ 7.35 (d, 2H), 7.28 (t, 2H), 7.17 (t, 1H), 4.61 (q, 1H), 2.67-2.62 (m, 1H), 1.81 (s, 3H), 1.71-1.50 (m, 8H), 1.27 (d, 3H); LCMS RtL=2.706 min; [M+H]+=216.2]

ORD 기록

ord-9b0c3d1f460d4baeaeb5a7d279f6f1b8

출처 데이터셋

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08742106B2