Benzylamine → N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide

HRID 491884Notes

Reaction equation

HRID 491884 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][C:13]([OH:15])=O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(Cl)(=O)C(Cl)=O.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.CN(C=O)C.C(N(CC)CC)C.CO>[CH2:22]([NH:29][C:13](=[O:15])[CH2:12][N:9]1[C:10](=[O:11])[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7]1=[O:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 3

HCID 7504BenzylamineHCID 20825N-PhthaloylglycineHCID 65578Oxalyl chloride

Product 1

HCID 277803N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a stirred solution of N-phthaloylglycine (11.92 g, 58 mmol) in dichloromethane (200 mL) at room temperature, oxalyl chloride (7.5 mL, 87 mmol) was added. To the reaction mixture was then added DMF (two drops). The reaction mixture was concentrated after stirring four hours at room temperature. Dichloromethane (100 mL, dry) was added; then benzylamine (9.5 mL, 87 mmol) was added slowly into the solution, followed by addition of triethylamine (12 mL, 87 mmol), slowly into the solution. Dichloromethane (200 mL) and methanol (50 mL) were then added, 30 min. after the completed addition of triethylamine. The reaction mixture was extracted with 2N HCl solution twice, 1N NaOH solution one time, and 1N HCl one time, then dried over MgSO4. The solution was filtered and concentrated to yield N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionDichloromethane (100 mL, dry) was added
  3. extractionThe reaction mixture was extracted with 2N HCl solution twice
  4. dry with material1N NaOH solution one time, and 1N HCl one time, then dried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-93855b5f2fd141848ec4796a7747cbe9
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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