N-(2-aminoethyl)acetamide → N-{2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-ethyl}-acetamide

HRID 431583Notes

Reaction equation

HRID 431583 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([C:17]([OH:19])=O)[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:34]([NH:37][CH2:38][CH2:39][NH2:40])(=[O:36])[CH3:35]>CN(C)C(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:11](=[CH:15][CH:16]=2)[C:12](=[O:14])[N:40]([CH2:39][CH2:38][NH:37][C:34](=[O:36])[CH3:35])[C:17]3=[O:19])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 66082N-(2-aminoethyl)acetamideHCID 682631,1'-CarbonyldiimidazoleHCID 223970954-(4-Fluoro-benzyloxy)-phthalic acid

Product 1

HCID 22397094N-{2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-ethyl}-acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-(4-fluoro-benzyloxy)-phthalic acid (185 mg, 0.64 mmol) and carbonyldiimidazole (109 mg, 0.67 mmol) in N,N-dimethylacetamide (3 mL) was stirred at room temperature for 10 min and then heated at 50° C. for 15 min. To this mixture was added N-acetylethylenediamine (78 mg, 0.76 mmol) and the resulting mixture heated under reflux for 20 min. After cooling to room temperature, the mixture was evaporated and the residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 98:2 to 9:1) to afford the title compound (139 mg, 62%) as an off-white solid. MS: m/e=357.3. (M+H+).

Workup

  1. temperatureheated at 50° C. for 15 min
  2. temperaturethe resulting mixture heated
  3. temperatureunder reflux for 20 min
  4. temperatureAfter cooling to room temperature
  5. customthe mixture was evaporated
  6. customthe residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 98:2 to 9:1)

Sources & evidence

ORD record
ord-e5b16f949dd1472b978f7b23ede30004
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

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