Hydrochloric Acid → 4'-(1-azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-3-amine Hydrochloride

HRID 969967Notes

Reaction equation

HRID 969967 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]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=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]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=3)=[CH:14][CH:15]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11300879HCID 11300879, compound

Product 1

HCID 694368684'-(1-azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-3-amine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1B (230 mg, 0.78 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 solid (210 mg, yield, 74%): 1H NMR (MeOH-d4, 300 MHz) δ 1.82-2.21 (m, 3H), 2.30-2.42 (m, 1H), 2.55-2.62 (m, 1H), 3.35-3.50 (m, 5H), 3.82-3.96 (m, 1H), 4.95-5.02 (m, 1H), 7.11 (dt, J=8.8, 2.0 Hz, 2H), 7.34 (ddd, J=9.1, 2.3, 1.3 Hz, 1H), 7.57-7.66 (m, 4H), 7.72 (ddd, J=7.8, 1.6, 1.0 Hz, 1H) ppm. MS (DCl/NH3) m/z 295 (M+H)+. Anal. Calculated for C19H22N2O.2.0HCl.0.2H2O: C, 61.52; H, 6.63; N, 7.55. Found: C, 61.22; H, 6.44; N, 7.38.

Sources & evidence

ORD record
ord-eb514ce8f9f34d718dead13323f1f69d
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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