Hydrochloric Acid → HCID 68611444, compound

HRID 2095417Notes

Reaction equation

HRID 2095417 reaction equation
[ClH:1].[NH:2]1[CH2:5][CH2:4][C@@H:3]1[CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]2)[CH:13]=1>CO.O>[ClH:1].[NH:2]1[CH2:5][CH2:4][C@@H:3]1[CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([N:14]2[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:18][CH2:19]2)[CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68611056HCID 68611056, compound

Product 1

HCID 68611444HCID 68611444, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Hydrochloric acid (2M, 0.77 mL, 4.5 equiv.) was added to a solution of 3-[(2(R)-azetidinyl)methoxy]-5-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]pyridine (130 mg, 0.34 mmol) in methanol/water (⅕ mL) under N2. The solution was stirred overnight at room temperature and lyophilized. The lyophilization process was repeated three times to afford the hydrochloride (150 mg) as a yellow solid. 1H NMR (D2O, 300 MHz) δ 7.93 (s, 1H), 7.78 (s, 1H), 7.45 (s, 1H), 7.34 (s, 5H), 4.92-4.87 (s, 1H), 4.48 (s, 2H), 4.43-4.41 (m, 2H), 4.10-3.99 (m, 2H), 3.78-3.73 (m, 2H), 3.59-3.55 (m, 2H), 2.97-2.89 (t, 2H, J=12.0 Hz), 2.62 (dd, 2H, J=8.4 Hz), 1.74-1.69 (m, 2H), 1.61-1.58 (m, 1H), 1.53-1.47 (m, 2H), 1.26-1.19 (m, 2H). LC-MS (ESI) m/z 382 (M+H+). Anal. Calcd. for C23H31N3O2.2.3HCl.1.45H2O: C, 56.21; H, 7.42; N, 8.55; Cl, 16.59. Found: C, 56.31; H, 7.63; N, 8.56; Cl, 16.75.

Sources & evidence

ORD record
ord-577ef6e932a54f839062ef3bdc0077df
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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