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

HRID 1382965

Reaction equation

HRID 1382965 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 141168944-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(1-ethyl-2-oxo-propoxy)-benzamideYield 20.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e66f7f589b6d4e17bb90f44fa34a51a3
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Linked notes

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