Sodium Chloride → 3-Pyridin-3-ylcyclohexanamine

HRID 571966ノート

反応式

HRID 571966 の反応式
Cl.[NH2:2]O.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][C:12](=O)[CH2:11]2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[Na+].[Cl-]>CO.O.C1COCC1>[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([NH2:2])[CH2:11]2)[CH:5]=1

参加物

10

反応物 6

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 221008783-(Pyridin-3-yl)cyclohexanone

生成物 1

HCID 594861283-Pyridin-3-ylcyclohexanamine

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Hydroxylamine hydrochloride (67.7 mg, 0.975 mmol) was added to a stirred mixture of 8c (122 mg, 0.696 mmol) and potassium carbonate (96.0 mg, 0.696 mmol) in MeOH (3.00 mL) and water (600 μl). After the reaction was deemed to be complete, the reaction mixture was partially concentrated in vacuo and partitioned between EtOAc and brine. The layers were separated, and the aq. layer was extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford a crude residue (m/z (ES) 191 (MH)+), which was dissolved in THF (3.50 mL) and cooled to 0° C. Lithium aluminum hydride (106 mg, 2.78 mmol) was added in several portions, and after the reaction was deemed to be complete, 1N NaOH was added. The resulting mixture was saturated with NaCl(s) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound, 8d. m/z (ES) 177 (MH)+

後処理

  1. concentrationthe reaction mixture was partially concentrated in vacuo
  2. custompartitioned between EtOAc and brine
  3. customThe layers were separated
  4. extractionthe aq. layer was extracted with EtOAc
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a crude residue (m/z (ES) 191 (MH)+), which
  9. extractionextracted with EtOAc
  10. dry with materialThe combined organics were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0259734d63c1445db1a13681ed9b5225
出典データセット
uspto-grants-2015_05
特許番号
US09029377B2

反応ノート

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