Ethyl [(phenoxycarbonyl)oxy]acetate → 2-(Ethyloxy)-2-oxoethyl 4-[(4-bromophenyl)oxy]-1-piperidinecarboxylate

HRID 2242933Notes

Reaction equation

HRID 2242933 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C1([O:21][C:22]([O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:22]([O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:21])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateHCID 126455664-(4-Bromophenoxy)piperidine

Product 1

HCID 674168332-(Ethyloxy)-2-oxoethyl 4-[(4-bromophenyl)oxy]-1-piperidinecarboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

2.7 g (7.58 mmol) of 4-[(4-bromophenyl)-oxy]piperidine, prepared in Step 4.2, and 1.70 g (7.6 mmol) of ethyl {[(phenyloxy)carbonyl]oxy}acetate, prepared in accordance with Example 1.1, are mixed in 40 ml of toluene and the solution is heated at 50° C. for 20 hours. After cooling, it is evaporated to dryness and the product is purified by chromatography on silica gel, eluting with a 40/60 mixture of ethyl acetate and cyclohexane. The eluate is subsequently triturated in diisopropyl ether, to give 2.9 g of product in powder form.

Workup

  1. customprepared in accordance with Example 1.1
  2. temperatureAfter cooling
  3. customit is evaporated to dryness
  4. customthe product is purified by chromatography on silica gel
  5. washeluting with a 40/60 mixture of ethyl acetate and cyclohexane
  6. customThe eluate is subsequently triturated in diisopropyl ether

Sources & evidence

ORD record
ord-81afad4f08c84058abee8c63369f8144
Source dataset
uspto-grants-2010_03
Patent number
US07674805B2

Reaction notes

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