[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:18][N:19](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN>O1CCCC1.ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:19][CH3:18])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1N-Benzyl 4-piperidinecarboxylic acid (5.00 g, 22.8 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (5.25 g, 27.4 mmol) and 1-hydroxybenzotriazole hydrate (3.84 g, 25.1 mmol) were added to a solution of methylamine (11.4 ml of a 2.0M solution in tetrahydrofuran, 22.8 mmol) in dichloromethane (100 ml). The mixture was stirred for 1 hour at room temperature, then partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to furnish a pale yellow solid, 3.50 g.
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