Water → HCID 43119952, compound

HRID 341777Notes

Reaction equation

HRID 341777 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:14]2[CH2:15][O:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 7835EpichlorohydrinHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 43119952HCID 43119952, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3.1 g piperidine-4-carboxylic acid ethyl ester, 6.4 ml epichlorohydrin and 0.1 g tetrabutyl-ammonium bromide in 15 ml toluene and 15 ml concentrated sodium hydroxide solution was stirred for 4 h at room temperature and subsequently admixed with 50 ml water. The organic phase was separated, the aqueous phase was shaken three times with 20 ml methylene chloride each time, the combined organic phases were dried over sodium sulfate and the solvent was removed in a vacuum. 2.1 g (rac)-1-oxiran-2-ylmethyl-piperidine-4-carboxylic acid ethyl ester was obtained. EI-MS: m/z 213 M+.

Workup

  1. customThe organic phase was separated
  2. stirringthe aqueous phase was shaken three times with 20 ml methylene chloride each time
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customthe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-c9b9bc86f9d84064b79107192e69f35c
Source dataset
uspto-grants-1999_01
Patent number
US05856309

Reaction notes

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