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

HRID 2088852Notes

Reaction equation

HRID 2088852 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. DMF (two drops) was then added. The resulting solution was concentrated after stirring four hours at room temperature. Dichloromethane (100 mL, dry) was then added to the residue. Benzylamine (9.5 mL, 87 mmol) was added slowly into the resulting solution. Triethylamine (12 mL, 87 mmol) was then added slowly into the solution. Dichloromethane (200 mL) and methanol (50 mL) were added 30 min after the completed addition of triethylamine. The resulting solution was extracted with 2 N HCl solution twice, 1 N NaOH solution one time and 1 N HCl one time, and 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 resulting solution was concentrated
  2. additionDichloromethane (100 mL, dry) was then added to the residue
  3. extractionThe resulting solution was extracted with 2 N HCl solution twice
  4. dry with material1 N NaOH solution one time and 1 N HCl one time, and then dried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e3570f2f9cf24b7483c00e94ff664eb9
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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