Hydrochloric Acid → N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-N-(4-methylthien-3-yl)amine Hydrochloride

HRID 1294676Notes

Reaction equation

HRID 1294676 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[C:21]([CH3:22])=[CH:20][S:19][CH:18]=3)=[CH:12][CH:11]=1)[CH2:2]2.[ClH:23].O1CCOCC1>C(OCC)(=O)C>[ClH:23].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17]3[C:21]([CH3:22])=[CH:20][S:19][CH:18]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11324489N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-N-(4-methylthien-3-yl)amine

Product 1

HCID 69520884N-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenyl]-N-(4-methylthien-3-yl)amine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 26A (198 mg, 0.57 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in 1,4-dioxane (0.5 mL, 2 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (155 mg, yield, 77%). 1H NMR (MeOH-d4, 300 MHz) δ 1.80–2.02(m, 2H), 2.03–2.16 (m, 4H), 2.30–2.38 (m, 1H), 2.46–2.55 (m, 1H), 3.20–3.47 (m, 5H), 3.72–3.80 (m, 1H), 4.68–4.75 (m, 1H), 6.66 (d, J=3.4 Hz, 1H), 6.83–6.99 (m, 5H) ppm. MS (DCl/NH3) m/z 315 (M+H)+. Anal. Calculated for C18H22N2OS.1.05HCl C, 61.29; H 6.59; N, 7.94. Found: C, 61.25; H, 6.50; N, 7.82.

Sources & evidence

ORD record
ord-11879ebd63ce4fac9b26844d061c8a00
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

Loading…