N-(2-tert-butoxybenzyl)-3-(4-phenylpiperidin-1-yl)-N-(pyridin-2-ylmethyl)propan-1-amine → 2-(((3-(4-Phenylpiperidin-1-yl)propyl)(pyridin-2-ylmethyl)amino)methyl)phenol
Reaction equation
C([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)(C)(C)C>CCOC(C)=O.Cl>[C:19]1([CH:16]2[CH2:15][CH2:14][N:13]([CH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:7]3[CH:32]=[CH:33][CH:34]=[CH:35][C:6]=3[OH:5])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:18][CH2:17]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Compound 20 (0.15 g, 0.31 mmol) was dissolved in 25 mL EtOAc saturated with HCl and stirred for 3 hr. The solvent was evaporated to dryness. The residue was purified on a silica gel TLC plate that was developed in 8% methanolic NH3 (7 M NH3 in methanol/92% CH2Cl2. The product was obtained as white solid (92%). 1H NMR (CDCl3) δ 8.589 (dd, 1H, Ar), 7.675 (ddd, 1H, Ar), 7.332 (d, 1H, Ar), 7.289 (ddd, 3H, Ar), 7.189 (m, 5H, Ar), 7.009 (dd, 1H, Ar), 6.854 (dd, 1H, Ar), 6.780 (ddd, 1H, Ar), 3.843 (s, 2H, —CH2—), 3.798, (s, 2H, —CH2—), 2.974 (d, 2H, —CH2—), 2.633 (t, 2H, —CH2—), 2.458 (m, 1H, —CH—), 2.333 (m, 2H, —CH2—), 2.000 (m, 2H, —CH2—), 1.782 (m (br), 6H). Mass Spec.=416.27 (M+H)+.
Workup
- customThe solvent was evaporated to dryness
- customThe residue was purified on a silica gel TLC plate that
Sources & evidence
- ORD record
- ord-5253f0e77a924818a0b7397643b10914
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08747810B2
Reaction notes
Loading…