Dimethylformamide → HCID 68912756, compound

HRID 732631Notes

Reaction equation

HRID 732631 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[C:12](=[O:15])([O-])[O-].[K+].[K+].BrCC(O[C:23]([CH3:26])([CH3:25])[CH3:24])=O.[CH3:27]N(C=O)C>C(OCC)C>[C:23]([C:12](=[O:15])[CH2:27][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 68912756HCID 68912756, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A 5.00 g portion of ethyl piperidine-4-carboxylate was dissolved in 100 ml of DMF, and 6.52 g of potassium carbonate and 6.74 g of tert-butyl bromoacetate were added thereto and stirred at 60° C. for 5Hours. After spontaneous cooling, the reaction solution was diluted with diethyl ether, washed with water and saturated brine and dried with anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 7.59 g of ethyl 1-(2-tert-butyl-2-oxoethyl)piperidine-4-carboxylate as a pale yellow oily substance.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe solvent was evaporated under a reduced pressure
  4. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-74f77cbc96e44ae8a074644f2cd87db5
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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