4-Aminophenol → 4-(3-(Dimethylamino)propoxy)aniline

HRID 1730913Notes

Reaction equation

HRID 1730913 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[H-].[Na+].[I-].[Na+].[CH3:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17][O:8][C:3]1[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=1

Participants

8

Reactant 5

HCID 4034-AminophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamine

Product 1

HCID 100584694-(3-(Dimethylamino)propoxy)aniline

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 65.4g (0.60 mole) of p-aminophenol in 250 ml of dimethylformamide is treated portion-wise with 28.6g (0.60 mole) of 50% sodium hydride. The temperature is maintained below 35° C during the addition, warmed to 70° C then cooled to 25° C. The mixture is treated with 5g of sodium iodide and 476 ml of a 1.89 N toluene solution of 3-dimethylaminopropyl chloride, then heated at 100°-105° C for 3 hours. The cooled mixture is poured over 500 ml of ice and extracted with 300 ml of ether (2 times). The combined solvent fractions are shaken in a separatory funnel with 150 ml of 6 N hydrochloric acid. The basic product is obtained by treating the aqueous fraction with 200g of potassium carbonate (ether extraction). After drying, the solvent is evaporated and the residue fractionated to give 25.1g of an oil, boiling point 128°-135° C/0.2 mm of Hg. (Continuation of the distillation yields 21.9g of di-alkylated material, boiling point 135°-158° C/0.2 mm of Hg).

Workup

  1. temperatureThe temperature is maintained below 35° C during the addition
  2. temperaturethen cooled to 25° C
  3. temperatureheated at 100°-105° C for 3 hours
  4. extractionextracted with 300 ml of ether (2 times)
  5. customThe basic product is obtained
  6. customAfter drying
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-cd3cdae3174f4db49a9b1cffabefa014
Source dataset
uspto-grants-1976_11
Patent number
US03994900

Reaction notes

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