Toluene → 2-[4-(Methyl-prop-2-ynyl-amino)-butyl]-isoindole-1,3-dione

HRID 374568Notes

Reaction equation

HRID 374568 reaction equation
BrCCCC[C:6]1[CH:16]=[CH:15][CH:14]=[C:8]2[C:9]([NH:11][C:12](=[O:13])[C:7]=12)=[O:10].[CH3:17][NH:18][CH2:19][C:20]#[CH:21].C(=O)([O-])[O-].[K+].[K+].[C:28]1([CH3:34])[CH:33]=[CH:32]C=CC=1>>[CH3:17][N:18]([CH2:19][C:20]#[CH:21])[CH2:32][CH2:33][CH2:28][CH2:34][N:11]1[C:12](=[O:13])[C:7]2[C:8](=[CH:14][CH:15]=[CH:16][CH:6]=2)[C:9]1=[O:10]

Participants

5

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 96160N-methylpropyn-2-ylamineHCID 21960043Bromobutylphthalimide

Product 1

HCID 153784972-[4-(Methyl-prop-2-ynyl-amino)-butyl]-isoindole-1,3-dione

Procedure

A mixture of bromobutylphthalimide (31.98 g, 0.113 mol), N-methyl-N-propargyl amine (8.19 g, 10 ml, 0.119 mol), potassium carbonate (23.39 g, 0.170 mol), and toluene (140 ml) was refluxed for 8 hours followed by overnight stirring at ambient temperature. The insoluble material was filtered off and washed with toluene. The flitrate and washings are evaporated to dryness, and the residue is purified by flash chromatography (Merck 60 silica gel, step gradient from 0-5% methanol in CH2Cl2). The pure fractions were combined, evaporated and dried in vacuo to yield the title compound, which was used as such in the next step.

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationThe insoluble material was filtered off
  3. washwashed with toluene
  4. customThe flitrate and washings are evaporated to dryness
  5. customthe residue is purified by flash chromatography (Merck 60 silica gel, step gradient from 0-5% methanol in CH2Cl2)
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8d3b30377b0d41268320a2f20a92a678
Source dataset
uspto-grants-1996_01
Patent number
US05480988

Reaction notes

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