1,4-Dibromobutane → N-(4-Bromobutyl)-3-methyl-3-n-propylglutarimide

HRID 2199045Notes

Reaction equation

HRID 2199045 reaction equation
[CH3:1][C:2]1([CH2:10][CH2:11][CH3:12])[CH2:8][C:7](=[O:9])[NH:6][C:4](=[O:5])[CH2:3]1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][N:6]1[C:7](=[O:9])[CH2:8][C:2]([CH3:1])([CH2:10][CH2:11][CH3:12])[CH2:3][C:4]1=[O:5]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 95853Glutarimide, 3-methyl-3-propyl-

Product 1

HCID 13232512N-(4-Bromobutyl)-3-methyl-3-n-propylglutarimideYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the IIa product prepared in Example 1 (25 g; 0.15 mole), 1,4-dibromobutane (33.5 g; 0.15 mole), and K2CO3 (40.6 g; 0.29 mole) was stirred for a period of 16 hrs in 250 mL refluxing acetonitrile. The inorganic solid was removed by filtration and the filtrate was concentrated to a oil which was distilled to give 42.5 g (95%) of a light yellow oil, b.p. 165°-190° at 0.09 mm.

Workup

  1. customThe inorganic solid was removed by filtration
  2. concentrationthe filtrate was concentrated to a oil which
  3. distillationwas distilled

Sources & evidence

ORD record
ord-9afa24540fd94ff9b5de32a0f4632172
Source dataset
uspto-grants-1982_11
Patent number
US04361565

Reaction notes

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