Hydrochloric Acid → 2-Chloro-5-[[2-(2-hydroxy-ethylamino)-ethylamino]-methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide dihydrochloride

HRID 1816034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816034
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][OH:30].[BH4-].[Na+].[ClH:33]>C(O)C.CO.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[ClH:1].[ClH:33].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][OH:30])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:5]

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 4311764Sodium borohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Produkt 1

HCID 98918542-Chloro-5-[[2-(2-hydroxy-ethylamino)-ethylamino]-methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.244 g, Example 1b), 2-(2-aminoethylamino)-ethanol (0.154 g), p-toluenesulfonic acid (0.005 g) and toluene (30 ml) were refluxed together under Dean-Stark conditions for 3hs, cooled and concentrated under reduced pressure to give an oil. This was dissolved in ethanol (30 ml) and cooled to 0 C. under a nitrogen atmosphere. Solid sodium borohydride (0.030 g) was added portionwise to this and the mixture stirred at room temperature for 30 min. The mixture was concentrated under reduced pressure and the residue purified by column chromatography over silica gel (eluting with 7:3:0.3 dichloromethane/methanol/35% aqueous ammonia) to give the free base. This was dissolved in methanol (10 ml) and treated with 4M hydrochloric acid in dioxane (4 ml) to give a solid precipitate. This was filtered off and washed with diethyl ether to afford the title compound as a solid (0.165 g).

Aufarbeitung

  1. temperaturewere refluxed together under Dean-Stark conditions for 3hs
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. temperaturecooled to 0 C
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customthe residue purified by column chromatography over silica gel (eluting with 7:3:0.3 dichloromethane/methanol/35% aqueous ammonia)
  8. customto give the free base
  9. customto give a solid precipitate
  10. filtrationThis was filtered off
  11. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8b142ba359534e06902693a4de7cbd5d
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06881754B2

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