Hydrochloric Acid → HCID 68612271, compound
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH2:25][C@@H:26]3[CH2:30][CH2:29][CH2:28][NH:27]3)[CH:23]=2)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:31]>CO.O>[ClH:31].[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH2:25][C@@H:26]3[CH2:30][CH2:29][CH2:28][NH:27]3)[CH:23]=2)[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-[3(S)-[3-(benzyloxy)propyl]-1-piperidinyl]-5-[(2(S)-pyrrolidinyl)methoxy]pyridine (160 mg, 0.39 mmol) in CH3OH (0.5 mL) was added 2 N hydrochloric acid (0.88 mL, 4.5 equiv.) at 0° C. under N2. The solution was stirred for 4 h at room temperature. Water (20 mL) was added, and the solution was lyophilized. The residue was dissolved in 12 mL of water and re-lyophilized. This process was repeated three times to afford the hydrochloride (189 mg) as a yellowish solid. 1H NMR (D2O, 300 MHz) δ 7.88 (d, 1H, J=2.1 Hz), 7.69 (d, 1H, J=1.8 Hz), 7.38-7.27 (m, 6H), 4.48 (narrow ABq, 2H), 4.44, 4.23 (ABq, 2H, JAB=10.5 Hz, low-field part d with J=3.3 Hz, high-field part d with J=7.5 Hz), 4.06 (m, 1H), 3.66 (m, 2H), 3.52 (t, 2H, J=6.3 Hz), 3.35 (t, 2H, J=7.2 Hz), 2.96 (td, 1H, J=10.5 (t), 3.0 Hz(d)), 2.69 (dd, 1H, J=10.5, 12.9 Hz), 2.29-2.17 (m, 1H), 2.16-1.97 (m, 2H), 1.96-1.76 (m, 2H), 1.76-1.42 (m, 5H), 1.37-1.08 (m, 3H). LC-MS (ESI) m/z 410 (M+H+). Anal. Calcd. for C25H35N3O2.2.5HCl.0.55H2O: C, 58.80; H, 7.62; N, 8.23. Found: C, 58.54; H, 7.89; N, 8.51.
Sources & evidence
- ORD record
- ord-661c55d17c8044f9a840224171d719e5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445684B2
Reaction notes
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