Hydrochloric Acid → 2-{2-[4-(4-Aminobutyl)phenoxy]ethylamino}acetamide dihydrochloride salt

HRID 1509863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1509863
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][CH2:22][C:23](=[O:25])[NH2:24])=[CH:14][CH:13]=1)(C)(C)C.[ClH:27]>C1COCC1.O1CCOCC1>[ClH:27].[ClH:27].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][CH2:22][C:23]([NH2:24])=[O:25])=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 58809802(4-{4-[2-(Carbamoylmethylamino)ethoxy]phenyl}butyl)carbamic acid tert-butyl ester

Produkt 1

HCID 668399752-{2-[4-(4-Aminobutyl)phenoxy]ethylamino}acetamide dihydrochloride salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Compound 3 (0.25 g, 0.68 mmol) was dissolved in THF (3 mL), treated with 4 N HCl in dioxane (10 mL) and the reaction was stirred at room temperature for 2 hours. After this time, TLC analysis indicated a complete reaction. The reaction mixture was concentrated under vacuum, and methanol (2 mL) was added to the resulting residue. The resulting precipitate was collected by vacuum filtration and further dried in a vacuum oven to provide 4 (0.154 g, 67% overall yield for two steps) as a light brown solid. 1H NMR (300 MHz, CD3OD) δ 1.70 (m, 4H), 2.65 (m, 2H), 2.95 (m, 2H), 3.27 (m, 2H), 3.52 (t, 2H), 3.90 (s, 2H), 4.30 (t, 2H), 6.92 (d, 2H), 7.18 (d, 2H). m/z (ESI) 266.

Aufarbeitung

  1. customa complete reaction
  2. concentrationThe reaction mixture was concentrated under vacuum, and methanol (2 mL)
  3. additionwas added to the resulting residue
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. customfurther dried in a vacuum oven
  6. customto provide
  7. custom4 (0.154 g, 67% overall yield for two steps) as a light brown solid

Quellen und Nachweise

ORD-Eintrag
ord-63f4a85769d14cfda1a9b7a5cbade9fc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211895B2

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