1-Chloro-4-(chloromethyl)benzene → n-Butyl 3-{4-[1-(4-chlorobenzyl)-piperazin-4-yl]-phenyl}-propionate

HRID 2290472Notes

Reaction equation

HRID 2290472 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1>C(#N)C>[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])=[CH:11][CH:12]=3)[CH2:6][CH2:5]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 20232520n-Butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate

Product 1

HCID 20232442n-Butyl 3-{4-[1-(4-chlorobenzyl)-piperazin-4-yl]-phenyl}-propionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 20.0 g. (68.8 mmole) n-butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate, 200 ml. acetonitrile, 10.4 g. (75.6 mmole) pulverised potassium carbonate and 12.2 g. (75.6 mmole) 4-chlorobenzyl chloride is heated for 36 hours at reflux temperature, filtered with suction and the filtrate evaporated. The residue is taken up in diethyl ether and the hydrochloride precipitated out by adding hydrogen chloride-containing diethyl ether. It is filtered off with suction, recrystallised from isopropanol and dried. Yield 29.0 g. (87% of theory) of hydrochloride; m.p. 222°-225° C.

Workup

  1. additionA mixture of 20.0 g
  2. temperatureat reflux temperature
  3. filtrationfiltered with suction
  4. customthe filtrate evaporated
  5. customthe hydrochloride precipitated out
  6. additionby adding hydrogen chloride-
  7. additioncontaining diethyl ether
  8. filtrationIt is filtered off with suction
  9. customrecrystallised from isopropanol
  10. customdried

Sources & evidence

ORD record
ord-4bf36cc9ef214493bd9e04f305e4d2b9
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

Loading…