1-(2-Hydroxyethyl)piperazine → 2-[3-[4-(2-Hydroxyethyl)-1-piperazinyl]propyl]-1H-isoindole-1,3(2H)-dione

HRID 1284622Notes

Reaction equation

HRID 1284622 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[OH:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C:8]3=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]3[C:6]2=[O:15])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 202522292-[3-[4-(2-Hydroxyethyl)-1-piperazinyl]propyl]-1H-isoindole-1,3(2H)-dioneYield 53.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of N-(3-bromopropyl)phthalimide (40.5 g) in acetone (375 ml) were added 1-(2-hydroxyethyl)piperazine (31.5 g) and potassium carbonate (63.0 g). The resulting mixture was refluxed with stirring for 3 hours. The reaction mixture was filtered and the filtrate was evaporated. The residual oil was subjected to column chromatography on silica gel, eluting with a mixture of chloroform and methanol (9:1). The fractions containing the object compound were collected and then evaporated to give an oil of N-[3-[4-(2-hydroxyethyl)-1-piperazinyl]propyl]phthalimide (25.5 g).

Workup

  1. temperatureThe resulting mixture was refluxed
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. washeluting with a mixture of chloroform and methanol (9:1)
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-703fff841cec4ac183d5ceb1451f1d3b
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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