Aniline → N-[4'-(1-azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-yl]-N-phenylamine

HRID 969983Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]3[CH:20]4[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]4)[CH2:16]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[N:17]12[CH2:22][CH2:21][CH:20]([CH2:19][CH2:18]1)[CH:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:3][CH:4]=3)=[CH:9][CH:10]=1)[CH2:16]2

Participants

Reactant 2

HCID 6115Aniline

HCID 69434105HCID 69434105, compound

Product 1

HCID 11222474N-[4'-(1-azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-yl]-N-phenylamine

Procedure

The product of Example 8A (405 mg, 1 mmol) was treated with aniline (110 mg, 1.2 mmol) according to the procedure in Example 8B. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.25) as solid (200 mg, yield, 54%). 1H NMR (MeOH-d4, 300 MHz) δ 1.42-1.56 (m, 1H), 1.62-1.88 (m, 2H), 1.99-2.12 (m, 1H), 2.14-2.22 (m, 1H), 2.73-3.02 (m, 5H), 3.27-3.38 (m, 1H), 4.51-4.59 (m, 1H), 6.80-6.87 (m, 1H), 6.94 (d, J=8.8 Hz, 2H), 7.06-7.15 (m, 4H), 7.18-7.26 (m, 2H), 7.44 (d, J=8.5 Hz, 2H), 7.49 (d, J=8.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 371 (M+H)+.

Workup

customThe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.25) as solid (200 mg, yield, 54%)

Sources & evidence

ORD record: ord-3dba003d23f04267a55aa2f5509e2f89
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07309699B2

Reaction notes

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