Diethylamine → HCID 19907377, compound

HRID 2371565Notes

Reaction equation

HRID 2371565 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:19]=[CH:18][C:11]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>CO>[CH2:20]([N:22]([CH2:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:19]=[CH:18][C:11]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=1)[CH3:21]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 19907354HCID 19907354, compound

Product 1

HCID 19907377HCID 19907377, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of methanol was added 2.1 g of methyl p-(6-bromohexyl)dihydrocinnamate and 4.67 g of diethylamine, and the mixture was refluxed for 5 hours. The solvent was evaporated off under a reduced pressure, 50 ml of ethyl acetate was added to the residue, and the mixture was washed twice with 20 ml of water, dried over magnesium sulfate and evaporated under a reduced pressure, to obtain 1.73 g of methyl p-(6-diethylaminohexyl)dihydrocinnamate as a colorless oil. To 1.5 g of this oil was added 4.7 ml of 1N sodium hydroxide aqueous solution, the mixture was stirred with heating at 85° C. for 3 hours, and water was evaporated off under a reduced pressure to obtain a residue, which was then dried in the presence of phosphorus pentaoxide under a reduced pressure to obtain 1.5 g of sodium p-(6-diethylaminohexyl)dihydrocinnamate. To 20 ml of dimethylformamide were added 1.4 g of the above salt and 0.86 g of diethylaminoethylchloride, and the reaction mixture was stirred for 4 hours at 60° C. After adding 50 ml of a saturated sodium chloride aqueous solution, the reaction mixture was extracted three times with 20 ml of ethyl acetate, and the extract was washed three times with water, dried over magnesium sulfate and evaporated under a reduced pressure to obtain 1.43 g of 2-diethylaminoethyl p-(6-diethylaminohexyl)dihydrocinnamate as a residue. Next, 1 g of this compound and 6 ml of ethyl iodide were added to 7 ml of ethanol, and the mixture was refluxed for 8 hours and allowed to stand in a freezer. The resulting crystal was recovered by filtration, washed twice with 10 ml of ethanol, and dried in the presence of phosphorus pentaoxide under a reduced pressure to obtain 0.8 g of the title compound as a colorless crystal.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customThe solvent was evaporated off under a reduced pressure, 50 ml of ethyl acetate
  3. additionwas added to the residue
  4. washthe mixture was washed twice with 20 ml of water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under a reduced pressure

Sources & evidence

ORD record
ord-6209fb556dee45c09e3d5d6e6814d00c
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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