1-Butanol → n-Butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate

HRID 2290471Notes

Reaction equation

HRID 2290471 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.[N+:17]([C:20]1[CH:34]=CC(C=CC(OCCCC)=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:41](O)[CH2:42]CC>[Pd]>[N:1]1([C:2]2[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]=2)[CH2:34][CH2:20][NH:17][CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 2631-Butanol2×HCID 11430Potassium CarbonateHCID 20232483n-Butyl 3-(4-aminophenyl)-propionateHCID 53427420n-Butyl 4-nitrocinnamate

Product 1

HCID 20232520n-Butyl 3-[4-(piperazin-1-yl)-phenyl]-propionate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 175 g. (0.79 mole) n-butyl 3-(-4-aminophenyl)-propionate (prepared by the hydrogenation of n-butyl 4-nitrocinnamate in the presence of palladiumcharcoal in n-butanol; b.p. 137°-138° C./0.013 mbar), 141.3 g. (0.79 mole) bis-(2-cholorethyl)-amine hydrochloride and 600 ml. n-butanol is maintained at reflux temperature for 48 hours, then 54.5 g. (0.39 mole) powdered potassium carbonate are added thereto and the reaction allowed to continue for a further 120 hours at the boiling temperature. Thereafter, the reaction mixture is suction filtered hot, the filtrate is evaporated in a vacuum and the oil remaining behind is taken up in n-butanol. The sulphate is now precipitated out in the cold by adding concentrated sulphuric acid. It is filtered off with suction, triturated with diethyl ether and dried. Yield 286.8 g. (69% of theory); m.p. 183°-185° C.

Workup

  1. additionA mixture of 175 g
  2. temperatureat reflux temperature for 48 hours
  3. additionare added
  4. filtrationfiltered hot
  5. customthe filtrate is evaporated in a vacuum
  6. customThe sulphate is now precipitated out in the cold
  7. additionby adding concentrated sulphuric acid
  8. filtrationIt is filtered off with suction
  9. customtriturated with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-2b41feae02964ea08b77d4529dff61ad
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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