o-Desmethyl metoclopramide → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(1-ethyl-2-oxo-propoxy)-benzamide

HRID 620266

Reaktionsgleichung

Reaktionsgleichung von HRID 620266
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([OH:19])[CH:3]=1.Br[CH:21]([CH2:25][CH3:26])[C:22](=[O:24])[CH3:23]>C(#N)C>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH:21]([CH2:25][CH3:26])[C:22](=[O:24])[CH3:23])[CH:3]=1

Komponenten

4

Edukt 2

HCID 9817332o-Desmethyl metoclopramideHCID 100122493-Bromo-2-pentanone

Produkt 1

HCID 141168944-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(1-ethyl-2-oxo-propoxy)-benzamideAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of the tetrabutylammonium salt of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (10.5 g, 20 mmoles) (from Prepration No. 3) in acetonitrile (150 ml) was treated with 3-bromo-2-pentanone (3.3 g of 80%, 20 mmoles, contaminated with 15% of 1-bromo-2-pentanone) [obtained according to the procedure of E. T. Borrows, D. O. Holland and J. Kenyon, J. Chem. Soc. 1083, (1946)]. After 3 hours, the solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried, and the solvent evaporated. The semisolid residue was triturated with ether to yield a solid which was recrystallized from ether--petroleum ether to yield 1.5 g of the title compound, mp. 75°-78°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.26 (s, 1H); 8.14 (bs, 1H); 6.1 (s, 1H); 4.5 (t, 1H); 4.4 (s, 2H); 3.69 (q, 2H); 2.64 (m, 6H); 2.1 (s, 3H); 2.1-1.7 (m, 2H); 1.05 (m, 9H).

Aufarbeitung

  1. customobtained
  2. customthe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water
  5. customdried
  6. customthe solvent evaporated
  7. customThe semisolid residue was triturated with ether
  8. customto yield a solid which
  9. customwas recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-a97e27bc5770454fa7262d9d3cf79a65
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04820715

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