Hydrochloric Acid → HCID 68611714, compound

HRID 2095357Notes

Reaction equation

HRID 2095357 reaction equation
[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C@H:20]([O:28][CH3:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=2)[CH:12]=1.[ClH:30]>CO>[ClH:30].[NH:1]1[CH2:4][CH2:3][C@H:2]1[CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C@H:20]([O:28][CH3:29])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59371410HCID 59371410, compound

Product 1

HCID 68611714HCID 68611714, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[(2(S)-azetidinyl)methoxy]-5-[3-(2(R)-methoxy-3-phenylpropyl)phenyl]pyridine (175 mg, 0.45 mmol) in methanol (1 mL) was added 2M hydrochloric acid (2 mL) at 0° C. under N2. The solution was stirred for 2 h at room temperature and evaporated. The residue was dissolved in 8 mL of water and lyophilized. The lyophilization process was repeated three times to give the hydrochloride (200 mg) as a colorless solid. 1H NMR (D2O, 300 MHz) δ 8.61 (s, 1H), 8.50 (s, 1H), 8.34 (s, 1H), 7.56-7.44 (m, 3H), 7.38-7.35 (m, 1H), 7.29-7.25 (m, 2H), 7.21-7.17 (m, 3H), 4.99-4.94 (m, 1H), 4.57 (d, 1H, J=3.9 Hz), 4.13-4.03 (m, 2H), 3.87-3.81 (m, 1H), 3.18 (s, 3H), 2.92-2.63 (m, 6H). LC-MS (ESI) m/z 389 (M+H+). Anal. Calcd. for C25H28N2O2.1.95HCl.1.15H2O: C, 62.51; H, 6.77; N, 5.83; Cl, 14.48. Found: C, 62.48; H, 6.82; N, 5.85; Cl, 14.48.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in 8 mL of water

Sources & evidence

ORD record
ord-c225a9e7a88349e0a210ea198d84fa13
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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