Dicyclohexylcarbodiimide → 2,5-Pyrrolidinedione, 1-[[(2,6-dimethyl-1-piperidinyl)acetyl]oxy]-

HRID 2364931Notes

Reaction equation

HRID 2364931 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[N:4]1[CH2:10][C:11]([OH:13])=[O:12].O[N:15]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]1=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[O:21]=[C:16]1[CH2:17][CH2:18][C:19](=[O:20])[N:15]1[O:12][C:11](=[O:13])[CH2:10][N:4]1[CH:3]([CH3:2])[CH2:8][CH2:7][CH2:6][CH:5]1[CH3:9]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 45790887HCID 45790887, compound

Product 1

HCID 111847332,5-Pyrrolidinedione, 1-[[(2,6-dimethyl-1-piperidinyl)acetyl]oxy]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.15 g (20 mMol) (2,6-dimethyl-piperidin-1-yl)-acetic acid hydrochloride (6), in 50 ml DMF, was added to 2.3 g (20 mMol) N-hydroxysuccinimide and 8.1 g (40 mMol) dicyclohexylcarbodiimide. The reaction mixture was stirred for 16 h at RT. The residue was filtered and the filtrate was evaporated under vacuum to dryness. After dissolving the residue in CH2Cl2, the solution was washed with NaHCO3, dried (sodium sulphate) and the solvent evaporated. The compound was then recrystallised from diisopropylether (A-Kohle).

Workup

  1. filtrationThe residue was filtered
  2. customthe filtrate was evaporated under vacuum to dryness
  3. dissolutionAfter dissolving the residue in CH2Cl2
  4. washthe solution was washed with NaHCO3
  5. dry with materialdried (sodium sulphate)
  6. customthe solvent evaporated
  7. customThe compound was then recrystallised from diisopropylether (A-Kohle)

Sources & evidence

ORD record
ord-349e8d589b1942019ff256b0e484ee08
Source dataset
uspto-grants-2014_04
Patent number
US08697604B2

Reaction notes

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