Hydrochloric Acid → 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 880001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 880001
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10]2[C:11]([C:16]3[CH:33]=[CH:32][C:19]4[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH2:24][C:18]=4[CH:17]=3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1.Cl>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10]2[C:11]([C:16]3[CH:33]=[CH:32][C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24][C:18]=4[CH:17]=3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 706652431,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Produkt 1

HCID 706649537-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (3.8 g) was dissolved in dioxane (20 ml). Gaseous hydrogen chloride was passed through the reaction mixture for 1.5 h. The reaction was monitored by TLC. On completion the solid formed was collected by filtration and washed with acetone. The solid was then dissolved in water and the mixture neutralised with aqueous sodium hydroxide (1M). The sticky solid formed was extracted with DCM. The organic phase was dried over sodium sulphate and concentrated in vacuo to give a solid. This was purified through silica, eluting the product with 0-12% methanol in DCM. The solid from this was triturated in diethyl ether to give the title compound, 2 g (69%) yield.

Aufarbeitung

  1. customOn completion the solid formed
  2. filtrationwas collected by filtration
  3. washwashed with acetone
  4. dissolutionThe solid was then dissolved in water
  5. customThe sticky solid formed
  6. extractionwas extracted with DCM
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. customThis was purified through silica
  11. washeluting the product with 0-12% methanol in DCM
  12. customThe solid from this was triturated in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f1960f1959ec4c669c17298e37c5f336
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993560B2

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