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

HRID 1989862Notes

Reaction equation

HRID 1989862 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 mol) was added to a mixture of intermediate (16) (0.0029 mol) in DCM (10 ml). The mixture was stirred overnight and then the solvent was evaporated. The residue was dissolved in DCM (10 ml). Methanol (10 ml) was added. The mixture was allowed to stand for 4 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 17, mp. 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 4 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-fe1eaf640413422ba170d18d91d75bad
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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