Hydrogen Bromide → 4-Ethoxycinnamoylpiperazine

HRID 1449155Notes

Reaction equation

HRID 1449155 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)[CH3:2].S(Cl)(Cl)=O.C(OC1C=CC(C=CC(Cl)=O)=CC=1)C.O.O.O.O.O.O.[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.Br>O1CCCC1.C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[CH:9][C:10]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[O:12])=[CH:13][CH:14]=1)[CH3:2]

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 24386Thionyl ChlorideHCID 120181Piperazine, hexahydrateHCID 2955753-(4-Ethoxyphenyl)prop-2-enoic acidHCID 53411295HCID 53411295, compound

Product 1

HCID 544061044-EthoxycinnamoylpiperazineYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 11.52 g. of 4-ethoxycinnamic acid and 10.71 g. of thionylchloride was prepared 4-ethoxycinnamoyl chloride, a solution of which in tetrahydrofuran was added gradually to a solution of 23.4 g. of piperazine hexahydrate, 20.67 g. of 47% hydrobromic acid and 90 ml. of ethanol. The resulting mixture was stirred overnight at room temperature and cooled with ice, the forming crystals being filtered off. The filtrate was condensed and treated just as in Reference example 1 to obtain 11.23 g. of the desired product (72% yield). The product was treated with concentrated hydrochloric acid to give the corresponding hydrochloride.

Workup

  1. temperaturecooled with ice
  2. filtrationthe forming crystals being filtered off
  3. customcondensed
  4. additiontreated just as in Reference example 1
  5. customto obtain 11.23 g

Sources & evidence

ORD record
ord-ca2480432f94430592653af21a5735a0
Source dataset
uspto-grants-1980_02
Patent number
US04189484

Reaction notes

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