Hydrochloric Acid → HCID 66731560, compound

HRID 1963158Notes

Reaction equation

HRID 1963158 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][N:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[ClH:21]>CO.[Pt](=O)=O>[ClH:21].[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:12][CH:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:18][CH2:19][NH:20]2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66732034HCID 66732034, compound

Product 1

HCID 66731560HCID 66731560, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(4-(methylsulfonyl)phenyl)isonicotinate (5.663 g, 19.44 mmol) was suspended in MeOH (20 mL) and hydrogen chloride (1.25 M in MeOH, 40 mL, 50.00 mmol) was added. The mixture was stirred at room temperature for 20 min and then evaporated in vacuo. The HCl salt was suspended in MeOH (100 mL) and platinum(IV) oxide (0.221 g, 0.97 mmol) added. The mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 2 h. The catalyst was filtered off and washed with MeOH. The filtrate was evaporated in vacuo yielding methyl 2-(4-(methylsulfonyl)phenyl)piperidine-4-carboxylate hydrochloride (5.84 g, 90%) as a white solid. MS m/z 298 (M+H)+

Workup

  1. customevaporated in vacuo
  2. customwas hydrogenated in a Büchi hydrogenator at room temperature
  3. wait5 bar for 2 h
  4. filtrationThe catalyst was filtered off
  5. washwashed with MeOH
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8176a4a818aa44a3ada6d94b7777037d
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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