1-芐基-3-哌啶甲酸乙酯性質(zhì)、用途與生產(chǎn)工藝
生產(chǎn)方法
向哌啶-3-甲酸乙酯（5.94 mL，38.24 mmol，1.0當量）的二氯甲烷（80 mL）和水（40 mL）混合溶液中，依次加入溴化芐（4.77 mL，1.05當量）和碳酸鈉（5.06 g，1.25當量）。將反應(yīng)混合物加熱回流3小時。反應(yīng)完成后，分離有機層，用飽和食鹽水洗滌，無水硫酸鎂干燥，減壓濃縮。殘余物通過硅膠快速柱色譜純化，以乙酸乙酯/己烷（1:6，v/v）為洗脫劑，得到1-芐基哌啶-3-甲酸乙酯（9），為無色油狀物，收率87%。
1H NMR (400 MHz, CDCl3) δ 7.29-7.18 (m, 5H, Ar-H), 4.11 (q, J = 7.2 Hz, 2H, OCH2CH3), 3.51 (d, J = 13.6 Hz, 1H, CHa-Ph), 3.44 (d, J = 13.2 Hz, 1H, CHb-Ph), 2.90 (m, 1H, 哌啶-H), 2.68 (m, 1H, 哌啶-H), 2.54 (m, 1H, 哌啶-H), 2.20 (m, 1H, 哌啶-H), 2.01 (m, 1H, 哌啶-H), 1.90 (m, 1H, 哌啶-H), 1.69 (m, 1H, 哌啶-H), 1.52 (m, 2H, 哌啶-H), 1.19 (t, J = 7.2 Hz, 3H, OCH2CH3);
13C NMR (62.5 MHz, CDCl3): δ 174.4, 138.4, 129.1, 128.2, 127.0, 63.3, 60.3, 55.5, 53.7, 42.0, 27.0, 24.6, 14.2;
HRESI-MS m/z calcd for [M + H]+ C15H22NO2: 248.1645, found: 248.1646.
參考文獻：
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 25, p. 5512 - 5532
[2] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 11235 - 11249
[3] Tetrahedron Letters, 2001, vol. 42, # 33, p. 5645 - 5649
[4] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 972 - 985
[5] Patent: US6664271, 2003, B1. Location in patent: Page column 15
1-芐基-3-哌啶甲酸乙酯
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