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

HRID 912738Notes

Reaction equation

HRID 912738 reaction equation
[C:1]1([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1([O:25][C:26]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([O:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:26]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:25])[CH2:17][CH2:18]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12094709Ethyl [(phenoxycarbonyl)oxy]acetateHCID 247000964-[(1-Naphthyloxy)methyl]piperidine

Product 1

HCID 674160052-(Ethyloxy)-2-oxoethyl 4-[(1-naphthalenyloxy)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2.75 g (11.4 mmol) of 4-[(1-naphthalenyloxy)methyl]piperidine, prepared in Step 7.2., and 2.56 g (11.4 mmol) of ethyl [(phenyloxy-carbonyl)oxy]acetate, prepared in accordance with Example 1.1, in 80 ml of toluene is heated at 50° C. overnight. It is evaporated to dryness and the residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution. The organic phase is decanted, dried over sodium sulfate and evaporated to dryness. The product is purified by chromatography on silica gel, eluting with a 50/50 mixture of cyclohexane and dichloromethane and then with dichloromethane and with a 95/5 mixture of dichloromethane and ethyl acetate. This gives 2.05 g of product in oil form, which is used as it is in the following step.

Workup

  1. customIt is evaporated to dryness
  2. additionthe residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution
  3. customThe organic phase is decanted
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe product is purified by chromatography on silica gel
  7. washeluting with a 50/50 mixture of cyclohexane and dichloromethane
  8. additionwith dichloromethane and with a 95/5 mixture of dichloromethane and ethyl acetate

Sources & evidence

ORD record
ord-2c69b4bff0ca4bb0be7ba54da775201e
Source dataset
uspto-grants-2011_09
Patent number
US08026258B2

Reaction notes

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