Potassium Carbonate → 2-Methoxy-4'-[3-(diethylamino)-propoxy]-alpha-ethyl-benzhydrol

HRID 364651Notes

Reaction equation

HRID 364651 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]([CH2:14][CH3:15])([OH:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[CH2:27]([N+:31](CCCC)([CH2:36][CH2:37]CC)[CH2:32][CH2:33]CC)[CH2:28][CH2:29]C.Cl.C(N(CC)CCCCl)C>C(C(C)=O)C(C)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]([CH2:14][CH3:15])([OH:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:29][CH2:28][CH2:27][N:31]([CH2:36][CH3:37])[CH2:32][CH3:33])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145749Diethylaminopropyl chloride, hydrochlorideHCID 2723671Tetrabutylammonium HydroxideHCID 14727321HCID 14727321, compound

Product 1

HCID 202395732-Methoxy-4'-[3-(diethylamino)-propoxy]-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

12.9 g. of 2-methoxy-4'-hydroxy-α-ethyl-benzhydrol are dissolved in 100 ml. of methyl isobutyl ketone, 23 g. of anhydrous potassium carbonate 0.4 ml. of a 40% tetrabutyl ammoniumhydroxide solution and 10.3 g. of 3-diethylamino-propyl chloride hydrochloride are added, and the solution is heated up to the boiling point. The reaction mixture is boiled for 4 hours, and the solvent is distilled off under reduced pressure. To the residue water is added, and it is extracted with benzene. The benzene phase is washed with a 5% potassium hydroxide solution and subsequently with water. After drying over anhydrous potassium carbonate, benzene is distilled off under reduced pressure, and the residue is fractionated in vacuo to yield 13.2 g. of the title compound, boiling at 200° to 203° C./13.3 Pa.

Workup

  1. temperaturethe solution is heated up to the boiling point
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionTo the residue water is added
  4. extractionit is extracted with benzene
  5. washThe benzene phase is washed with a 5% potassium hydroxide solution and subsequently with water
  6. dry with materialAfter drying over anhydrous potassium carbonate, benzene
  7. distillationis distilled off under reduced pressure
  8. customto yield 13.2 g

Sources & evidence

ORD record
ord-e0b56837ae5643779e5db1a46ccc4680
Source dataset
uspto-grants-1986_08
Patent number
US04605672

Reaction notes

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