Diethylamine → N,N-diethyl-4-(hydroxymethyl)benzamide

HRID 895606Notes

Reaction equation

HRID 895606 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35]>CN(C)C=O.O>[CH2:34]([N:36]([CH2:37][CH3:38])[C:7]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:11][CH:10]=1)=[O:9])[CH3:35]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 763604-(Hydroxymethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58586323N,N-diethyl-4-(hydroxymethyl)benzamideYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxymethylbenzoic acid (10.0 g) was dissolved in N,N-dimethylformamide (200 ml), added with 1-hydroxybenzotriazole (9.766 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC.HCl, 13.855 g) and stirred at room temperature for 1 hour. The reaction mixture was added with diethylamine (13.6 ml) and further stirred at room temperature for 1 hour. The reaction mixture was added with water (200 ml) and extracted twice with dichloromethane (200 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:2) to obtain 12.80 g of the title compound. Yield: 94%.

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. extractionextracted twice with dichloromethane (200 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-738aa043be834859924adc43bad5437a
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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