Pipecolic Acid → Methyl pipecolinate

HRID 1287284Notes

Reaction equation

HRID 1287284 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:14][O-].[Na+]>CO.CCOCC>[C:3]([CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][NH:1]1)([O:5][CH3:14])=[O:4]

Participants

6

Reactant 3

HCID 849Pipecolic AcidHCID 24386Thionyl ChlorideHCID 10942334Sodium Methoxide

Product 1

HCID 3463753Methyl pipecolinateYield 85.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

A slurry of 26 g (0.20 mole) of pipecolinic acid in 100 ml of methanol is cooled to -10° and 16.7 ml (0.22 mole) of thionyl chloride added over 5 minutes. The slurry is allowed to warm to ambient temperature and stirred overnight whereupon a thick slurry forms. Addition of 300 ml of methanol gives a solution which is evaporated in vacuo. The residue is suspended in 100 ml in methanol, treated with a solution of 10.8 g (0.2 mole) of sodium methoxide in 100 ml of methanol, and diluted with 400 ml of ether. The solid which forms is filtered and the filtrate evaporated and redissolved in ether. Filtration, evaporation and solution are repeated three times and the final residue distilled in vacuo to give 24.6 g (85%) of the above titled ester, bp. 70°-70.5° at 4.0 mm.

Workup

  1. customgives a solution which
  2. customis evaporated in vacuo
  3. filtrationThe solid which forms is filtered
  4. customthe filtrate evaporated
  5. dissolutionredissolved in ether
  6. filtrationFiltration, evaporation and solution
  7. distillationthe final residue distilled in vacuo

Sources & evidence

ORD record
ord-1b0ad927ff194025a50b4c57fcc61c60
Source dataset
uspto-grants-1976_10
Patent number
US03984419

Reaction notes

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