4-Bromoanisole → HCID 53726868, compound

HRID 1980143Notes

Reaction equation

HRID 1980143 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.O1CCCC1.[C:16]([CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)(=O)C>[OH:23][C:16]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 77304-BromoanisoleHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 23326073HCID 23326073, compound

Product 1

HCID 53726868HCID 53726868, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 15 parts of magnesium, 112.2 parts of 1-bromo-4-methoxybenzene and 540 parts of tetrahydrofuran, was added dropwise a solution of 80 parts of ethyl 4-benzoyl-1-piperidinecarboxylate in 360 parts of tetrahydrofuran at reflux temperature. Upon completion, stirring was continued for 2 hours at reflux. After cooling overnight, the reaction mixture was poured onto a mixture of 300 parts of crushed ice and 40 parts of acetic acid at 10° C. After stirring for 15 minutes, the layers were separated. The organic layer was dried, filtered and evaporated. The residue was taken up in methylbenzene and the latter was evaporated. The residue was suspended three times in 70 parts of 2,2'-oxybispropane and the latter was decanted each time. The residue was evaporated to dry, yielding 106 parts of ethyl 4-[hydroxy(4-methoxyphenyl)phenylmethyl]-1-piperidinecarboxylate as a residue (intermediate 31).

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. temperatureat reflux temperature
  4. stirringUpon completion, stirring
  5. temperatureat reflux
  6. temperatureAfter cooling overnight
  7. stirringAfter stirring for 15 minutes
  8. customthe layers were separated
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. customevaporated
  12. customthe latter was evaporated
  13. customthe latter was decanted each time
  14. customThe residue was evaporated
  15. customto dry

Sources & evidence

ORD record
ord-d0622a9e41824fb0a7f8dec3a17cbf0f
Source dataset
uspto-grants-1984_11
Patent number
US04485107

Reaction notes

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