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

HRID 1382965

Reaktionsgleichung

Reaktionsgleichung von HRID 1382965
[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 Preparation 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 etherpetroleum ether to yield 1.5 g of the title compound, mp. 75°-78°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ8.26 (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, 6 H); 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 etherpetroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-e66f7f589b6d4e17bb90f44fa34a51a3
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04808624

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