Hydrochloric Acid → HCID 69519169, compound

HRID 1294660Notes

Reaction equation

HRID 1294660 reaction equation
[I:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:12]3[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]3)[CH2:8]2)=[CH:4][CH:3]=1.[ClH:17].O1CCOCC1>C(OCC)(=O)C>[ClH:17].[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:12]3[CH2:11][CH2:10][N:9]([CH2:14][CH2:13]3)[CH2:8]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 210726043-(4-Iodophenoxy)-1-azabicyclo[2.2.2]octane

Product 1

HCID 69519169HCID 69519169, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 14A (3.7 g, 11.2 mmol) in ethyl acetate (50 mL) was treated with 4M HCl in 1,4-dioxane (5 mL, 20 mmol). The title compound was obtained as a solid (4.0 g, yield, 98%). 1H NMR (MeOH-d4, 300 MHz) δ 1.80–2.20 (m, 3H), 2.30–2.40 (m, 1H), 2.50 (m, 1H), 3.30–3.48 (m, 5H), 3.76 (m, 1H), 4.92 (m, 1H), 6.80 (d, J=9.1 Hz, 2H), 7.61 (d, J=8.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 330 (M+H)+. Anal. calculated for C13H16INO.1.0HCl: C, 42.70; H, 4.69; N, 3.83. Found: C, 42.72; H, 4.61; N, 3.65.

Sources & evidence

ORD record
ord-26d9999e53e64f48b940fb1ccbbe3d52
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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