2-Bromotoluene → Ethyl 1-benzylpiperidine-4-carboxylate

反応式

[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[CH2:19]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1

参加物

実験手順

A mixture of ethyl isonipecotate (69.25 g, 0.441 mol). -bromotoluene (75.44 g, 52.4 ml, 0.441 mol) and triethylamine (44.74 g, 61.5 ml, 0.441 mol) in 1000 ml methylene chloride was stirred at r.t. for 20 hr. The mixture was washed with brine and the organic layer was separated, dried and concentrated to give 97.016 g of ethyl 1-benzylpiperidine-4-carboxylate as a yellow oil. HNMR (CDCl)δ 1.2(t, 3H), 1.6-1.9 (m, 4H), 2.0 (dt, 2H), 2.2-2.3 (m, 1H), 2.85 (m, 2H), 3.5 (s, 2H), 4.1 (q, 2H), 7.2-7.36 (m, 5H) ppm.