Dichloromethane → Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate

HRID 846742Notes

Reaction equation

HRID 846742 reaction equation
[C:1]1([CH2:7][O:8][CH:9]2[C:14](=[O:15])[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.[C:26](Cl)(=[O:30])[O:27][CH2:28][CH3:29]>C(N(CC)CC)C>[O:15]=[C:14]1[CH2:13][CH2:12][N:11]([C:26]([O:27][CH2:28][CH3:29])=[O:30])[CH2:10][CH:9]1[O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10928Ethyl chloroformateHCID 15096753HCID 15096753, compound

Product 1

HCID 3019711Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred mixture of 10 parts of 3-(phenylmethoxy)-1-(phenylmethyl)-4-piperidinone and 65 parts of dichloromethane were added dropwise 5 parts of ethyl carbonochloridate at room temperature. After stirring for 6.30 hours at reflux, there were added 5 parts of N,N-diethylethanamine. Upon completion, stirring at reflux was continued for 24 hours. The reaction mixture was washed successively with water, a diluted hydrochloric acid solution and again with water, dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 8.1 parts (86.5%) of ethyl 4-oxo-3-(phenylmethoxy)-1-piperidinecarboxylate as an oily residue (intermediate 47).

Workup

  1. temperatureat reflux
  2. stirringUpon completion, stirring
  3. temperatureat reflux
  4. waitwas continued for 24 hours
  5. washThe reaction mixture was washed successively with water
  6. dry with materiala diluted hydrochloric acid solution and again with water, dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column-chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

Sources & evidence

ORD record
ord-f1663116453c4c75aed1d5bdd25dcaf3
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

Loading…