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

HRID 1809560Notes

Reaction equation

HRID 1809560 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.CN(C=O)C.[Cl:22]N1C(=O)CCC1=O>[Cl-].[Na+].O>[Cl:22][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 3

HCID 6228DimethylformamideHCID 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 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A 250 mL flask was charged with tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (2.0 g, 8.8 mmol) and DMF (100 mL). 1-chloropyrrolidine-2,5-dione (1.2 g, 8.8 mmol) was added and stirred at ambient temperature overnight. The reaction was poured into 1:1 brine:water and extracted with EtOAc. The organic layer was washed twice with water, dried over sodium sulfate, filtered and concentrated to afford tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate (2.3 g, 100%).

Workup

  1. extractionwater and extracted with EtOAc
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e30fc72fc48a4cea800efdb408739fa7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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