Aluminum(III) Chloride → 6-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromide

HRID 1649244Notes

Reaction equation

HRID 1649244 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[BrH:1].[N:13]1([C:10]2[CH:9]=[C:8]3[C:7](=[CH:12][CH:11]=2)[NH:6][C:4](=[O:5])[CH2:3][CH2:2]3)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 20480598N-(beta-bromopropionyl)-p-piperazinylaniline

Product 1

HCID 132363086-(1-Piperazinyl)-3,4-dihydrocarbostyril hydrobromideYield 40.9%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A suspension of 2.2 g of N-(β-bromopropionyl)-p-piperazinylaniline and 28 g of pulverized anhydrous aluminum chloride in 50 ml of carbon disulfide was stirred under reflux for 4 hours. The reaction mixture was poured into ice water and the precipitations were collected by filtration, washed with water and then with ether and converted to hydrobromic acid salt followed by recrystallization from methanol-water to give 0.9 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril monohydrobromide, m.p. 289°-293° C. (decomp.) (methanol-water), colorless needles.

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe precipitations
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customfollowed by recrystallization from methanol-water

Sources & evidence

ORD record
ord-e9fd5df792fe4e5383eff38c698f793b
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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