1-(4-Chlorobenzyl)-4-[[(N-Boc-valyl)amino]methyl]piperidine → 1-(4-Chlorobenzyl)-4-[(valylamino)methyl]piperidine
Reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH:17]C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1>Cl.CO>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15](=[O:28])[C@H:16]([CH:25]([CH3:27])[CH3:26])[NH2:17])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
1-(4-Chlorobenzyl)-4-[{(N-Boc-valyl)amino}methyl]piperidine (1.1 g, 2.51 mmol) was dissolved in 3 M HCl-CH3OH solution (25 mL) and stirred at 25° C. for 1 h. The reaction mixture was concentrated and the resulting salt was dissolved in 3:1 tBuOH—H2O (25 mL). Anion (OH−) exchange resin was added until the solution was slightly basic. Filtration and concentration afforded 1(4-chlorobenzyl)-4-{(valylamino)methyl}piperidine (819 mg, 97%) which required no further purification: RPLC (97%); ESI/MS 338.1 (M++H, C19H28ClN3O).