N-Carbethoxyphthalimide → Phthalimide

HRID 2264885Notes

Reaction equation

HRID 2264885 reaction equation
C(OC(OCC)CCCN)C.C([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(OCC)=O>CC#N>[C:21]1(=[O:22])[NH:17][C:18](=[O:27])[C:19]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]12

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 806724,4-Diethoxybutylamine

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-aminobutyraldehyde diethyl acetal 1a (89.3 mmol) in CH3CN (100 mL) was added N-carbethoxyphthalimide (93.8 mmol). Once the reaction was complete, the acetonitrile was removed under reduced pressure and the aqueous phase extracted with EtOAc (×3). The organic phase were combined, then washed with water (×4), saturated brine (×3), then dried (Na2SO4), filtered, and evaporated under reduced pressure to give the title compound 1b, which crystallized on standing.

Workup

  1. customthe acetonitrile was removed under reduced pressure
  2. extractionthe aqueous phase extracted with EtOAc (×3)
  3. washwashed with water (×4), saturated brine (×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ece6f6c5ad2f44a69b4ba65e5c1c1976
Source dataset
uspto-grants-2010_12
Patent number
US07855295B2

Reaction notes

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