Piperazine → N-[4-(1-Piperazinyl)butyl]-3,3-dimethylglutarimide

HRID 2199046Notes

Reaction equation

HRID 2199046 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]1=[O:15].CC1(C)CC(=O)NC(=O)C1.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:26]1([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]2=[O:15])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 142924,4-Dimethylpiperidine-2,6-dioneHCID 136603351-(4-Bromobutyl)-4,4-dimethylpiperidine-2,6-dione

Product 1

HCID 20516935N-[4-(1-Piperazinyl)butyl]-3,3-dimethylglutarimideYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(4-bromobutyl)-3,3-dimethylglutarimide (20.0 g; 0.07 mole [prepared from 3,3-dimethylglutarimide using the method of Example 2]); piperazine (31.0 g; 0.36 mole); K2CO3 (29.8 g; 0.22 mole); and KI (0.1 g) was refluxed in 250 mL acetonitrile for 18 hr. The mixture was filtered, concentrated and the unreacted piperazine removed by vacuum sublimation. The residual material was distilled to yield 17.2 g (85%) product, b.p. 170°-178° C. at 0.01 mm.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe unreacted piperazine removed by vacuum sublimation
  4. distillationThe residual material was distilled

Sources & evidence

ORD record
ord-613b4dba2a814f92b4367ed0edb4cfd4
Source dataset
uspto-grants-1982_11
Patent number
US04361565

Reaction notes

Loading…