4-Piperidinecarboxylic acid → HCID 14252917, compound

HRID 1860391Notes

Reaction equation

HRID 1860391 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].[CH2:12]([O:15][C:16](Cl)=[O:17])[CH:13]=[CH2:14]>C(Cl)Cl>[CH2:12]([O:15][C:16]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:17])[CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium Hydroxide2×HCID 18052Allyl chloroformate

Product 1

HCID 14252917HCID 14252917, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 4-piperidincarboxylic acid (25 g) in dry DCM (30 ml) a solution of NaOH 2N (207 ml) was added. The reaction mixture was then cooled to 0-5° and a solution of allylchloroformate (22 ml) in DCM (1 ml) was added over 40 min. The reaction was stirred at 0-5° C. for 2 h, then NaOH 2N (40 ml) was added and the organic phase was separated. The aqueous phase was washed with DCM, then acidified with H2SO4 conc. (10 ml) to pH2 and extracted with EA. The organic layer was washed with brine, dried and the solvent removed in vacuo to give the title compound as a colourless oil (39.5 g).

Workup

  1. temperatureThe reaction mixture was then cooled to 0-5°
  2. customthe organic phase was separated
  3. washThe aqueous phase was washed with DCM
  4. extractionextracted with EA
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-24f57aa01bfd4ca888832e1c0acaba26
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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