Potassium Carbonate → n-Butyl 3-{4-[1-(4-chlorophenyl)-piperazin-4-yl]-phenyl}-propionate

HRID 2290473Notes

Reaction equation

HRID 2290473 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])=[CH:4][CH:3]=1.Cl[CH2:18][CH2:19][N:20]([CH2:28][CH2:29]Cl)[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([N:20]2[CH2:28][CH2:29][N:1]([C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])=[CH:6][CH:7]=3)[CH2:18][CH2:19]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95112Aniline, p-chloro-N,N-bis(2-chloroethyl)- (8CI)HCID 20232483n-Butyl 3-(4-aminophenyl)-propionate

Product 1

HCID 20232689n-Butyl 3-{4-[1-(4-chlorophenyl)-piperazin-4-yl]-phenyl}-propionate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 12.3 g. (55 mmole) n-butyl 3-(4-aminophenyl)-propionate, 16.0 g. (55 mmole) N,N-bis-(2-chloroethyl)-4-chloroaniline and 50 ml. n-butanol is maintained at reflux temperature for 48 hours, then 3.8 g. (27 mmole) pulverised anhydrous potassium carbonate are added thereto and stirring continued for 1 week at reflux temperature. Thereafter, it is suction filtered hot, the filtrate is evaporated in a vacuum and the residue is stirred with ligroin and suction filtered. The product is now taken up in diethyl ether, filtered and mixed with hydrogen chloride-containing diethyl ether. Since the hydrochloride is difficult to suction filter, the ether phase is evaporated in a vacuum and the residue recrystallised from n-butanol. Yield 9.5 g. (39% of theory) of hydrochloride; m.p. 179°-183° C. (decomp.).

Workup

  1. additionA mixture of 12.3 g
  2. temperatureat reflux temperature for 48 hours
  3. additionare added
  4. waitcontinued for 1 week
  5. temperatureat reflux temperature
  6. filtrationfiltered hot
  7. customthe filtrate is evaporated in a vacuum
  8. stirringthe residue is stirred with ligroin and suction
  9. filtrationfiltered
  10. filtrationfiltered
  11. additionmixed with hydrogen chloride-
  12. additioncontaining diethyl ether
  13. filtrationto suction filter
  14. customthe ether phase is evaporated in a vacuum
  15. customthe residue recrystallised from n-butanol

Sources & evidence

ORD record
ord-79b09a8cbda04c408288e3347f25ef64
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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