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

HRID 570089Notes

Reaction equation

HRID 570089 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]>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

4

Reactant 2

HCID 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

12.60 g (60 mMol) (2,6-Dimethyl-piperidin-1-yl)-acetic acid hydrochloride (5), in 100 ml DMF, was added to 7.02 g (60 mMol) N-hydroxysuccinimide and 12.58 g (60 mMol) N,N-dicyclohexylcarbodiimide. The reaction mixture was stirred for 16 h at RT. The residue was filtered and the filtrate was evaporated in vacuo to dryness. After dissolving the residue in 300 ml CH2Cl2, the solution was washed with NaHCO3, dried over sodium sulphate and the solvent was evaporated. The compound was then recrystallised from diisopropylether (activated charcoal).

Workup

  1. filtrationThe residue was filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionAfter dissolving the residue in 300 ml CH2Cl2
  4. washthe solution was washed with NaHCO3
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was evaporated
  7. customThe compound was then recrystallised from diisopropylether (activated charcoal)

Sources & evidence

ORD record
ord-88bdae61eb98419aa9d5aff4c9fe1234
Source dataset
uspto-grants-2015_05
Patent number
US09023656B2

Reaction notes

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