N-Methylbenzylamine → HCID 69434355、化合物

HRID 969979ノート

反応式

HRID 969979 の反応式
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

参加物

7

反応物 3

HCID 7669N-MethylbenzylamineHCID 23676156Sodium t-butoxideHCID 69434105HCID 69434105、化合物

生成物 1

HCID 69434355HCID 69434355、化合物

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-234b213f2e1146b7a09c47f3d40a911b
出典データセット
uspto-grants-2007_12
特許番号
US07309699B2

反応ノート

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