Potassium Carbonate → 3-(4-benzylpiperidin-1-yl)-N-(2-tert-butoxybenzyl)-N-(pyridin-2-ylmethyl)propan-1-amine
Reaction equation
[C:1]([O:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[CH2:8][N:9]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2].[CH2:36](C1CCNCC1)C1C=CC=CC=1.C(OC1C=CC=CC=1CN(CC1C=CC=CN=1)CCCCl)(C)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:19]([CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]2[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=2[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:14][CH2:15]1)[C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:36]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The same procedure as described for compound 20 was applied to 4-benzyl piperidin (0.30 g, 1.73 mmol), compound 19 (0.4 g, 1.15 mmol), KI (0.57 g, 3.45 mmol) and K2CO3 (0.79 g, 5.75 mmol). The residue was redissolved in CH2Cl2 and chromatographed on a silica-gel column with the following eluents: 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as yellow oil (64% yield). 1H NMR (CDCl3) δ 8.453 (dd, 1H, Ar), 7.576 (ddd, 1H, Ar), 7.516 (m, 2H, Ar), 7.224 (m, 2H, Ar), 7.135 (m, 1H, Ar), 7.075 (m, 4H, Ar), 6.982 (m, 2H, Ar), 3.730 (s, 2H, —CH2—), 3.655 (s, 2H, —CH2—), 2.864 (d, 2H, —CH2—), 2.482 (t, 4H, —CH2—CH2—), 2.324 (t, 2H, —CH2—), 1.888 (t, 2H, —CH2—), 1.728 (p, 2H, —CH2—), 1.586 (d, 2H, —CH2—), 1.502 (m, 1H, —CH—), 1.324 (s, 9H, —C(CH3)3), 1.288 (overlapped m, 2H, —CH2—). Mass Spec.=486.35 (M+H)+.
Workup
- customchromatographed on a silica-gel column with the following eluents
Sources & evidence
- ORD record
- ord-d5602439f1e342639c0375fe25d43cc2
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08747810B2
Reaction notes
Loading…