Chlorosuccinimide → Tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate

HRID 1972160Notes

Reaction equation

HRID 1972160 reaction equation
[OH:1][N:2]=[CH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[Cl:17]N1C(=O)CCC1=O>CN(C=O)C.[Cl-].[Na+].O>[Cl:17][C:3](=[N:2][OH:1])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 72698249Tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate

Product 1

HCID 76573117Tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

tert-Butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (2.0 g, 8.8 mmol) in DMF (100 mL) was charged with 1-chloropyrrolidine-2,5-dione (1.2 g, 8.8 mmol). The reaction stirred at ambient temperature overnight. The material was poured into a 1:1 brine:water mixture and the resultant solution was extracted with ethyl acetate. The organic layer was wash twice with water, dried, and concentrated to afford the title compound (2.3 g, 100%).

Workup

  1. extractionwater mixture and the resultant solution was extracted with ethyl acetate
  2. washThe organic layer was wash twice with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c55278570d34b45a67ffe51c33d71ff
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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