HCID 66731716, compound → HCID 66732206, compound

HRID 1963138Notes

Reaction equation

HRID 1963138 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1>CO.C(Cl)Cl.[Pt](=O)=O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 66731716HCID 66731716, compound

Product 1

HCID 66732206HCID 66732206, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-chlorophenyl)isonicotinate hydrochloride (4.46 g, 15.69 mmol) was dissolved in MeOH (40 mL) and platinum(IV) oxide (0.356 g, 1.57 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated leaving a brown solid. The solid was dissolved in DCM and washed with 1 M K2CO3 and brine. The organic layer was dried through a phase-separator and evaporated. The residue was dissolved in DCM and added onto SCX-2 cation exchange columns (4*10 g columns. Each column was washed with DCM, MeOH and then eluted with NH3/MeOH (1 CV each). The NH3/MeOH layer was evaporated yielding methyl 2-(4-chlorophenyl)piperidine-4-carboxylate (3.13 g, 79%). MS m/z 254 (M+H)+

Workup

  1. customwas hydrogenated in a Büchi hydrogenator at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH
  4. customthe eluate evaporated
  5. customleaving a brown solid
  6. washwashed with 1 M K2CO3 and brine
  7. customThe organic layer was dried through a phase-separator
  8. customevaporated
  9. dissolutionThe residue was dissolved in DCM
  10. additionadded onto SCX-2 cation exchange columns (4*10 g columns
  11. washEach column was washed with DCM, MeOH
  12. washeluted with NH3/MeOH (1 CV each)
  13. customThe NH3/MeOH layer was evaporated

Sources & evidence

ORD record
ord-936771f1b5194c42a4c12559b283d90d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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