Hydrochloric Acid → HCID 66732187, compound

HRID 1963231Notes

Reaction equation

HRID 1963231 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:17]>CO.[Pt](=O)=O>[ClH:17].[CH:1]1([CH:7]2[CH2:8][CH:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][NH:16]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12183945Methyl 2-Phenylisonicotinate2×

Product 1

HCID 66732187HCID 66732187, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst5×HCID 887MethanolSolvent3×

Procedure

Methyl 2-phenylisonicotinate (3.182 g, 14.92 mmol) (from reference compound 34, step 1) was dissolved in MeOH (30 mL) and hydrogen chloride (1.25 M in MeOH, 14.33 mL, 17.91 mmol) was added. The solvents were evaporated to give a slightly yellow solid. The residue was dissolved in MeOH (60 mL) and platinum(IV) oxide (0.102 g, 0.45 mmol) was added. The resulting mixture was then hydrogenated in a Büchi hydrogenator at 8 bar for 5 h. More platinum(IV) oxide (121 mg) was added and the hydrogenation continued overnight at 8 bar (15 h). Platinum(IV) oxide (120 mg) was added and the hydrogenation continued at 60 C for 5 hours. Platinum(IV) oxide (120 mg) was added and the hydrogenation was continued at 60 C overnight (15 h). The reaction mixture was filtered through diatomic earth containing filter carton and washed with methanol. The solvents were evaporated and the residue dried in vacuum to give a white solid. The residue was redissolved in MeOH (60 mL). Platinum(IV) oxide (340 mg) was added and the hydrogenation continued at 8 bar, 60 C overnight (22 h). The reaction mixture was filtered through diatomic earth containing filter carton and washed with methanol. The solvents were evaporated and the residue dried in vacuum to give methyl 2-cyclohexylpiperidine-4-carboxylate hydrochloride (3.50 g, 89%) as a white solid. MS m/z 226 (M+H)+

Workup

  1. customThe solvents were evaporated
  2. customto give a slightly yellow solid
  3. waitthe hydrogenation continued overnight at 8 bar (15 h)
  4. waitthe hydrogenation continued at 60 C for 5 hours
  5. customwas continued at 60 C overnight (15 h)
  6. filtrationThe reaction mixture was filtered through diatomic earth
  7. additioncontaining
  8. filtrationfilter carton
  9. washwashed with methanol
  10. customThe solvents were evaporated
  11. customthe residue dried in vacuum
  12. customto give a white solid
  13. customcontinued at 8 bar, 60 C overnight (22 h)
  14. filtrationThe reaction mixture was filtered through diatomic earth
  15. additioncontaining
  16. filtrationfilter carton
  17. washwashed with methanol
  18. customThe solvents were evaporated
  19. customthe residue dried in vacuum

Sources & evidence

ORD record
ord-616108def7dd4f5f82debbad57a285cc
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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