Potassium Carbonate → Methyl 4-[1-(benzenesulphonyl)-piperazin-4-ylmethyl]-benzoate

HRID 2290451Notes

Reaction equation

HRID 2290451 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:13]1([S:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:13]1([S:19]([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=3)[CH2:24][CH2:23]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 8087121-(Benzenesulfonyl)piperazine

Product 1

HCID 8743532Methyl 4-[1-(benzenesulphonyl)-piperazin-4-ylmethyl]-benzoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 11.5 g. (50 mmole) methyl 4-bromomethylbenzoate, 11.3 g. (50 mmole) 1-benzenesulphonylpiperazine, 6.91 g. (50 mmole) powdered potassium carbonate and 100 ml. butan-2-one is maintained at reflux temperature for 20 hours, then suction filtered while hot and the filtrate evaporated. After cooling, the product is filtered off with suction and recrystallised from methanol to give 11.6 g. (62% of theory) of the desired product; m.p. 145°-146° C.

Workup

  1. additionA mixture of 11.5 g
  2. temperatureat reflux temperature for 20 hours
  3. filtrationsuction filtered while hot and the filtrate
  4. customevaporated
  5. temperatureAfter cooling
  6. filtrationthe product is filtered off with suction
  7. customrecrystallised from methanol
  8. customto give 11.6 g

Sources & evidence

ORD record
ord-3b0bc9d052a841da8602a09a7a0a9eea
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

Loading…