Hydrochloric Acid → 4-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acid

HRID 1760191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760191
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]CC)=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20750053HCID 20750053, Verbindung

Produkt 1

HCID 220370584-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acidAusbeute 146 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of ethyl (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetate (13.0 g, 42.8 mmol) in methanol (150 mL) was treated with an aqueous solution of sodium hydroxide (3 N, 30 mL, 90 mmol) and heated at reflux for 2 hours. The solution was cooled to room temperature and neutralized with the addition of concentrated hydrochloric acid (12 N, 7.5 mL). The solvent was evaporated in vacuo, and the resultant amorphous solid was dried in vacuo with heating (˜50° C.) overnight to give (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetic acid (17.2 g) which was used in the subsequent step without purification. MS m/z 304 (MH+); NMR(DMSO-d6): δ 1.74 (br d, 2 H), 2.53-2.67 (m, 2 H), 2.74-2.86 (m, 2 H), 3.33 (s, 2 H), 4.29-4.42 (m, 1 H), 6.97-7.05 (m, 3 H) and 7.38-7.43 (m, 1 H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. customwas dried in vacuo
  5. temperaturewith heating (˜50° C.) overnight

Quellen und Nachweise

ORD-Eintrag
ord-b028b8350e4d4411abb02f9a1b95112d
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06841552B1

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