Triethylamine → HCID 18367365, compound

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Cl.C(N(CC)CC)C>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

Procedure

A solution of ethyl 2-piperidinecarboxylate (10.0 ml), 3-methoxybenzyl chloride (9.2 ml), and triethylamine (26.6 ml) in N,N-dimethylformamide (64.0 ml) was stirred at room temperature overnight and partitioned between ethyl acetate and water. The organic layer was separated, washed with water (four times) and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford ethyl 1-(3-methoxybenzyl)-2-piperidinecarboxylate (12.06 g) as a colorless oil. (+) APCI-MS (m/z): 278 (M+ +1) IR (Film): 1725, 1600, 1260 cm-1NMR (CDCl3, δ): 1.29 (3H, t, J=7.1 Hz), 1.50-1.85 (6H, m), 2.10-2.22 (1H, m), 2.88-3.00 (1H, m), 3.14 (1H, dd, J=6.8, 5.2 Hz), 3.40 (1H, d, J=13.4 Hz), 3.78 (1H, d, J=13.4 Hz), 3.81 (3H, s), 4.21 (2H, q, J=7.1 Hz), 6.77-6.82 (1H, m), 6.89-6.93 (2H, m), 7.17-7.27 (1H, m)