Water → Benzamide

HRID 19994

Reaktionsgleichung

Reaktionsgleichung von HRID 19994
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:9].[K+].C(Cl)(Cl)Cl.O>C(O)(C)(C)C>[C:1]([NH2:8])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6212ChloroformHCID 7505BenzonitrileHCID 14797Potassium Hydroxide

Produkt 1

HCID 2331Benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A sample of 3-[(2-dimethylamino)methyl]-1-hydroxycyclohexyl]-benzonitrile (Procedure A, 1.66 g, 6.4 mmol) as a mixture of diastereomers was dissolved in tert-butanol (20 mL), powdered potassium hydroxide (1.8 g, 32.1 mmol) was added, and the reaction was brought to reflux for 1 h. After cooling the reaction, chloroform (50 mL) and water (50 mL) were added. The organic layer was separated, dried (K2CO3), filtered, and concentrated to afford 3-[(2-dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide as a diastereomeric mixture (1.6 g, 93%). The mixture was purified on a reverse phase C-18 column with 0.5% ammonium acetate in water and acetonitrile as eluents. Compound 1, 3-[(1-RS, 2-SR)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide, eluted first. Next to elute was Compound 2, 3-[(1-RR, 2-SS)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]-benzamide.

Aufarbeitung

  1. temperatureto reflux for 1 h
  2. temperatureAfter cooling
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried (K2CO3)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f96448cc915d417a9196344c71f92d38
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745492B2

Verknüpfte Notizen

Wird geladen…