Hydrochloric Acid → HCID 11529767, compound

HRID 2358035Notes

Reaction equation

HRID 2358035 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][CH3:20])[CH2:16][CH:17]=1.Cl>CO.[Pt]=O>[Cl:1][C:2]1[C:7]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67532979HCID 67532979, compound

Product 1

HCID 11529767HCID 11529767, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[2-chloro-3-(methylsulfonyl)phenyl]-1-propyl-1,2,3,6-tetrahydropyridine (0.46 g, 1.47 mmol), platinum oxide (0.11 g) and hydrochloric acid (0.1 ml, conc) in methanol (30 ml) was hydrogenated at 50 psi for 1 h under hydrogen gas. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and evaporated to dryness to give 0.48 g of crude product as the hydrochloric acid salt. Purification by flash column chromatography (ethylacetate/methanol, 1:1) gave the title compound (0.35 g, 75%). The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 250-252° C. MS m/z (relative intensity, 70 eV) 315 (M+, 3), 288 (37), 287 (15), 286 (bp) 129 (7).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customevaporated to dryness
  4. customto give 0.48 g of crude product as the hydrochloric acid salt
  5. customPurification by flash column chromatography (ethylacetate/methanol, 1:1)

Sources & evidence

ORD record
ord-b934717bae934164b109f4f4dd0ea039
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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