Hydrochloric Acid → 1-[5-(Undecylamino)hexyl]-3,7-dimethylxanthine

HRID 1419780

Reaktionsgleichung

Reaktionsgleichung von HRID 1419780
C([BH3-])#N.[Na+].O=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14].[CH2:25]([NH2:36])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].Cl.[Cl-].[NH4+].[OH-].[NH4+]>O1CCCC1.CO>[CH2:25]([NH:36][CH:7]([CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:13]1=[O:14])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 81742UndecylamineHCID 5003444Sodium cyanoborohydrideHCID 186910651-(6-Oxohexyl)-3,7-dimethylxanthine

Produkt 1

HCID 538807901-[5-(Undecylamino)hexyl]-3,7-dimethylxanthineAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (63 mg, 1.0 mmol) was added to a mixture of 1-(6-oxohexyl)-3,7-dimethylxanthine (150 mg, 0.5 mmol), undecylamine (0.43 mL, 2.5 mmol), 38% aqueous hydrochloric acid solution (0.2 mL, 2.5 mmol), methanol (5 mL), and tetrahydrofuran (5 mL). The resulting mixture was stirred for 48 hours. Saturated aqueous ammonium chloride solution (20 mL) was added to the stirred mixture, followed by an additional 20 minutes of stirring and addition of 30% aqueous ammonium hydroxide solution (30 mL). The mixture was extracted with 25% methanol-dichloromethane (3×mL) and the combined extracts dried over sodium sulfate. The solvents were evaporated under vacuum, resulting in 190 mg of 1-[5-(Undecylamino)hexyl]-3,7-dimethylxanthine (86% yield).

Aufarbeitung

  1. waitfollowed by an additional 20 minutes
  2. stirringof stirring
  3. extractionThe mixture was extracted with 25% methanol-dichloromethane (3×mL)
  4. dry with materialthe combined extracts dried over sodium sulfate
  5. customThe solvents were evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ffac374c5524058a407cf5d5fafef18
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889011

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