Hydrochloric Acid → HCID 68610538, compound

HRID 2095400Notes

Reaction equation

HRID 2095400 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 59371616HCID 59371616, compound

Product 1

HCID 68610538HCID 68610538, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[1-[5-[(2(S)-pyrrolidinyl)methoxy]-3-pyridyl]-3(R)-pyrrolidinyl]-1-propanol (120 mg, 0.39 mmol) in methanol (0.3 mL) was added 2N hydrochloric acid (0.64 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 (150 mg) as a light-yellow solid. 1H NMR (D2O, 300 MHz) δ 7.56 (s, 1H), 7.53 (s, 1H), 6.95 (s, 1H), 4.44 (d, 1H, J=10.5 Hz), 4.24 (t, 1H, J=8.1 Hz), 4.06-4.04 (m, 1H), 3.57-3.26 (m, 7H), 2.92 (t, 1H, J=8.7 Hz, 1H), 2.32-1.98 (m, 5H), 1.97-1.83 (m, 1H), 1.68-1.54 (m, 5H). LC-MS (ESI) m/z 306 (M+H+). Anal. Calcd. for C17H27N3O2.2.3HCl.1.0H2O: C, 50.13; H, 7.75; N, 10.32. Found: C, 50.15; H, 7.85; N, 10.20.

Workup

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

Sources & evidence

ORD record
ord-a01943ffc4cb422e91defea8c052524c
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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