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

HRID 912733Notes

Reaction equation

HRID 912733 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.[CH2:15]([O:17][C:18](=[O:30])[CH2:19][O:20][C:21](OC1C=CC=CC=1)=[O:22])[CH3:16]>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:21]([O:20][CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:30])=[O:22])[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. temperatureAfter cooling
  2. customit is evaporated to dryness
  3. customthe product is purified by chromatography on silica gel
  4. washeluting with a 40/60 mixture of ethyl acetate and cyclohexane
  5. customThe eluate is subsequently triturated in diisopropyl ether

Sources & evidence

ORD record
ord-54127f7df42041928360b671e0e9b566
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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