Trifluoroacetic acid → HCID 57640336, compound
Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:28][N:21]([CH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (2.7 ml, 35 mmol) is added to a solution of 4-{(3-methyl-butyl)-[(thiazol-2-yl)-methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.55 mmol) in dichloromethane (2.7 ml). The reaction is stirred for 1 hour at room temperature. The reaction is concentrated, loaded onto a SCX-2 (5 g) column, and washed with water (50 ml) and methanol (50 ml). The product is then eluted off with 2M ammonia in methanol (100 ml) and concentrated on a rotary evaporator to yield (0.14 g) of N-(3-methylbutyl)-N-[(1,3-thiazol-2-yl)methyl]piperidin-4-amine: mass spectrum (ion spray): m/z=268 (M+1); 1H NMR (CDCl3): δ=7.67 (1H, d), 7.22 (1H, d), 3.95 (2H, s), 3.16-3.09 (2H, m), 2.67-2.49 (5H, m), 1.81 (2H, brd), 1.69-1.57 (2H, m), 1.50-1.32 (4H, m), 0.87 (6H, d).