Hydrochloric Acid → HCID 67207426, compound

HRID 1894388Notes

Reaction equation

HRID 1894388 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)(=[O:4])=[O:3].C(O)C.[ClH:17]>O1CCOCC1.[Pt]=O>[ClH:17].[ClH:17].[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 672062154-(3-Methanesulfonyl-propyl)-pyridine

Product 1

HCID 67207426HCID 67207426, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 312751,4-DioxaneSolvent

Procedure

In a round bottom of flask was charged with 4-(3-methanesulfonyl-propyl)-pyridine (373 mg) and ethanol (5 mL). Hydrochloric acid was added (1 mL, 4N solution in dioxane) with stirring. The mixture was concentrated then the residue was taken in methanol and water. Platinum oxide (21 mg, 0.09 mmol, Aldrich) was added, and the mixture was hydrogenated at 60 psi overnight using a Parr apparatus. Upon completion, the mixture was filtered through Celite and washed thoroughly with methanol. The filtrate was concentrated to give 4-(3-methanesulfonyl-propyl)-piperidine dihydrochloride as a white solid (480.7 mg, 85% pure). The crude product was used without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customwas hydrogenated at 60 psi overnight
  3. filtrationUpon completion, the mixture was filtered through Celite
  4. washwashed thoroughly with methanol
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7711d4e7935b4cc298d0c8c8ad46ab27
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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