Hydrochloric Acid → N-Nitrosopipecolic acid

HRID 2216563Notes

Reaction equation

HRID 2216563 reaction equation
Cl.[N:2]([O-:4])=O.[Na+].[CH2:6]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[NH:9][CH2:8][CH2:7]1>O>[N:2]([N:9]1[CH2:8][CH2:7][CH2:6][CH2:11][CH:10]1[C:12]([OH:14])=[O:13])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 849Pipecolic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 20614N-Nitrosopipecolic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Conc. HCl (1.96 mL) and NaNO2 (2.2 g) were added to the H2O (21 mL) solution of DL-pipecolic acid (3.04 g) under a nitrogen atmosphere at 0° C. and stirred for 1 h. The solution was extracted with CH2Cl2 and organic layer was washed with brine. The mixture was dried over Na2SO4 and concentrated under reduced pressure to afford crude (2RS)-1-nitrosopiperidine-2-carboxylic acid as pale yellow crystals.

Workup

  1. extractionThe solution was extracted with CH2Cl2 and organic layer
  2. washwas washed with brine
  3. dry with materialThe mixture was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fcb67382cbe4463a5d1a5cfb5e26890
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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