Dichloromethane → (+/-)-Methyl 1-(4-nitrophenyl)-alpha-phenyl-4-piperidineacetate

HRID 490867Notes

Reaction equation

HRID 490867 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([OH:23])=[O:22])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH2:30](Cl)Cl>>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:21]([O:23][CH3:30])=[O:22])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 22499400(+/-)-1-(4-Nitrophenyl)-alpha-phenyl-4-piperidineacetic acid

Product 1

HCID 22499408(+/-)-Methyl 1-(4-nitrophenyl)-alpha-phenyl-4-piperidineacetate

Procedure

Thionyl chloride (0.01 mole) was added to a mixture of intermediate (13) (0.0029 mole) in DCM (10 ml). The mixture was stirred for one minute overnight and then allowed to stand. The solvent was evaporated. The residue was dissolved in DCM (10 ml). Methanol (10 ml) was added. The mixture was allowed to stand for four hours, then poured out into a NaHCO3 solution and extracted with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was triturated in hexane/DIPE. The precipitate was filtered off and dried, yielding 0.9 g of (±)-methyl 1-(4-nitrophenyl)-α-phenyl-4-piperidineacetate (intermediate 14, melting point 124° C.).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in DCM (10 ml)
  3. additionMethanol (10 ml) was added
  4. waitto stand for four hours
  5. additionpoured out into a NaHCO3 solution
  6. extractionextracted with DCM
  7. customThe organic layer was separated
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was triturated in hexane/DIPE
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-52d0c57cc580469caf04444c4b60d636
Source dataset
uspto-grants-2009_05
Patent number
US07528154B2

Reaction notes

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