Hydrochloric Acid → N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]pyridin-3-amine Dihydrochloride

HRID 1294667Notes

Reaction equation

HRID 1294667 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:12][CH:11]=1)[CH2:2]2.[ClH:23].O1CCOCC1>C(OCC)(=O)C>[ClH:23].[ClH:23].[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11426435N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]pyridin-3-amine

Product 1

HCID 69519673N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]pyridin-3-amine Dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 19A (110 mg, 0.37 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in 1,4-dioxane (0.5 mL, 2 mmol). The title compound was obtained as a solid (130 mg, yield, 96%). 1H NMR (MeOH-d4, 300 MHz) δ 1.85–2.18 (m, 3H), 2.25–2.40 (m, 1H), 2.50–2.58 (m, 1H), 3.30–3.50 (m, 5H), 3.78–3.8(m, 1H), 4.92 (m, 1H), 7.08 (dt, J=8.9, 3.7 Hz, 2H), 7.26 (dt, J=9.2, 3.7 Hz, 2H), 7.78 (dd, J=8.9, 5.5 Hz, 1H), 7.93 (ddd, J=8.8, 2.7, 1.4 Hz, 1H), 8.06 (dt, J=5.4, 1.0 Hz, 1H), 8.17 (d, J=3.1 Hz, 1H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. Anal. Calculated for C18H21N3O.2.0HCl.1.1H2O: C, 55.70; H, 6.54; N, 10.83. Found: C, 55.55; H, 6.28; N, 11.09.

Sources & evidence

ORD record
ord-fba69011c251450e86ea938c56492486
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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