N-Methylbenzylamine → HCID 69434355, compound

HRID 969979Notes

Reaction equation

HRID 969979 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.[CH2:23]([NH:30][CH3:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[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]([N:30]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:31])=[CH:3][CH:4]=3)=[CH:9][CH:10]=1)[CH2:16]2

Participants

7

Reactant 3

HCID 7669N-MethylbenzylamineHCID 23676156Sodium t-butoxideHCID 69434105HCID 69434105, compound

Product 1

HCID 69434355HCID 69434355, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

The product of Example 8A (405 mg, 1 mmol) in toluene (5 mL) was treated with benzyl(methyl)amine (Aldrich, 146 mg, 1.2 mmol), Pd2(dba)3 (Strem Chemicals, 24 mg, 0.025 mmol), (tBu3P)2Pd (Strem Chemicals, 26 mg, 0.05 mmol), tBuONa (Aldrich, 105 mg 1.1 mmol) and heated at 110° C. under N2 for 15 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate (20 mL), and washed with brine (2×5 mL). The organic phase was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.35) as a solid (200 mg, yield, 50%). 1H NMR (MeOH-d4, 300 MHz) showed a mixture of the title compound and 3-(biphenyl-4-yloxy)-1-aza-bicyclo[2.2.2]octane as solid (200 mg). MS (DCl/NH3) m/z 399 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with brine (2×5 mL)
  3. concentrationThe organic phase was concentrated
  4. customthe title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.35) as a solid (200 mg, yield, 50%)
  5. additiona mixture of the title compound and 3-(biphenyl-4-yloxy)-1-aza-bicyclo[2.2.2]octane as solid (200 mg)

Sources & evidence

ORD record
ord-234b213f2e1146b7a09c47f3d40a911b
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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