Hydrochloric Acid → HCID 68612216, compound

HRID 2095405Notes

Reaction equation

HRID 2095405 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15]2)[CH:11]=[N:12][CH:13]=1.[ClH:23]>CO>[ClH:23].[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([N:14]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15]2)[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59371376HCID 59371376, compound

Product 1

HCID 68612216HCID 68612216, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[1-[5-[(2(S)-pyrrolidinyl)methoxy]-3-pyridyl]-3(S)-pyrrolidinyl]-1-propanol (200 mg, 0.66 mmol) in methanol (0.5 mL) was added 2N hydrochloric acid (1.1 mL, 3.3 equiv.) under N2. The reaction mixture was stirred for 4 h at room temperature. After evaporation in vacuo, the residue was diluted with water (12 mL) and lyophilized. The lyophilization process was repeated three times to obtain the hydrochloride (210 mg) as a light-yellow solid. 1H NMR (D2O, 300 MHz) δ 7.57 (s, 1H), 7.54 (s, 1H), 6.95 (s, 1H), 4.51 (d, 1H, J=10.5 Hz), 4.24 (t, 1H, J=9.0 Hz), 4.07-4.05 (m, 1H), 3.57-3.26 (m, 7H), 2.93 (t, 1H, J=9.0 Hz, 1H), 2.33-1.99 (m, 5H), 1.98-1.84 (m, 1H), 1.69-1.55 (m, 5H). LC-MS (ESI) m/z 306 (M+H+). Anal. Calcd. for C17H27N3O2.5.2HCl: C, 41.25; H, 6.56; N, 8.49. Found: C, 41.35; H, 6.64; N, 8.34.

Workup

  1. customAfter evaporation in vacuo
  2. additionthe residue was diluted with water (12 mL)

Sources & evidence

ORD record
ord-2581ba016fb7473cb58afd4544e6cb4f
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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