Pentane → 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(4-diethylamino-4-oxobutoxy)benzamide

HRID 620277Notes

Reaction equation

HRID 620277 reaction equation
CCCCC.[H-].[Na+].[NH2:8][C:9]1[C:24]([Cl:25])=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[O:14])=[C:11]([OH:26])[CH:10]=1.Cl[CH2:28][CH2:29][CH2:30][C:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:32]>CN(C=O)C.[Cl-].[Na+].O>[NH2:8][C:9]1[C:24]([Cl:25])=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22])=[O:14])=[C:11]([O:26][CH2:28][CH2:29][CH2:30][C:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:32])[CH:10]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 24348694-Chloro-N,N-diethyl-butyramideHCID 9817332o-Desmethyl metoclopramide

Product 1

HCID 200595024-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(4-diethylamino-4-oxobutoxy)benzamideYield 79.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a well-stirred suspension of pentane-washed sodium hydride (0.52 g of 60%, 3 mmole) in 3 ml dry DMF was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (3.43 g, 12 mmoles) (prepared as Example 53). To this was added 10 ml of DMF and the mixture was stirred at ambient temperature for 45 minutes then warmed to about 50° C. for 15 minutes whereupon 4-chloro-N,N-diethylbutyramide (1.92 g, 11 mmoles) was added. The mixture was then stirred at 60°-70° C. for 6 hours, at room temperature for 2 days and then at 60°-70° C. for a further 4 hours. After cooling, the mixture was poured into 400 ml of brine and extracted with methylene chloride (4×100 ml). After combining, the organic phase was washed two times with 100 ml of 10% aqueous sodium hydroxide and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give an oil (3.75 g). This was purified by flash chromatography on silica gel to give 1.64 g of the title compound as an oil.

Workup

  1. additionwas added
  2. stirringThe mixture was then stirred at 60°-70° C. for 6 hours, at room temperature for 2 days
  3. waitat 60°-70° C. for a further 4 hours
  4. temperatureAfter cooling
  5. extractionextracted with methylene chloride (4×100 ml)
  6. washthe organic phase was washed two times with 100 ml of 10% aqueous sodium hydroxide and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56c8ea2de0474cde9a70b613c5bf8d51
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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