Potassium Carbonate → Ethyl 4-{2-[1-(4-methoxybenzyl)-piperazin-4-yl]-ethyl}-benzoate

HRID 2290455Notes

Reaction equation

HRID 2290455 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.Br[CH2:17][CH2:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:17][CH2:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH2:10][CH2:9]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2319051-((4-Methoxyphenyl)methyl)piperazineHCID 12748305Ethyl 4-(2-bromoethyl)benzoate

Product 1

HCID 20232583Ethyl 4-{2-[1-(4-methoxybenzyl)-piperazin-4-yl]-ethyl}-benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 250 ml. butan-2-one, 15.47 g. (75 mmole) 1-(4-methoxybenzyl)-piperazine, 19.3 g. (75 mmole) ethyl 4-(2-bromoethyl)-benzoate and 20.7 g. (0.15 mole) powdered potassium carbonate is maintained at reflux temperature for 60 hours, then suction filtered while hot and the filtrate evaporated in a vacuum. After the addition of diethyl ether, the product crystallises, the yield being 17.5 g. (61% of theory) of the desired product; m.p. 75°-76° C. The hydrochloride is precipitated from the filtrate by means of hydrogen chloride-containing diethyl ether. After recrystallisation from aqueous ethanol, there are obtained 7.6 g. (23% of theory) of the desired product; m.p. 280°-281° C.

Workup

  1. additionA mixture of 250 ml
  2. temperatureis maintained
  3. temperatureat reflux temperature for 60 hours
  4. filtrationsuction filtered while hot and the filtrate
  5. customevaporated in a vacuum
  6. additionAfter the addition of diethyl ether
  7. customthe product crystallises
  8. customThe hydrochloride is precipitated from the filtrate by means of hydrogen chloride-
  9. additioncontaining diethyl ether
  10. customAfter recrystallisation from aqueous ethanol, there
  11. customare obtained 7.6 g

Sources & evidence

ORD record
ord-ad4ff06baa074ce5a6d8f6066e76210c
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

Loading…