Hydrochloric Acid → HCID 17895683, compound

HRID 2263509Notes

Reaction equation

HRID 2263509 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=1.Cl>CO.[Pt]=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57438799HCID 57438799, compound

Product 1

HCID 17895683HCID 17895683, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(2,3-dichlorophenyl)-1,2,3,6-tetrahydropyridine (0.49 g, 2.15 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. Aqueous sodium carbonate (10%, 50 ml) was added. The aqueous phase was extracted with ethylacetate (3×30 ml) and the combined organic phases was dried (MgSO4), filtered and evaporated to dryness. Yield: 0.17 g. MS m/z (rel. intensity, 70 eV) 230 (M+, 22), 229 (24), 228 (35), 196 (30), 194 (bp).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customevaporated to dryness
  4. additionAqueous sodium carbonate (10%, 50 ml) was added
  5. extractionThe aqueous phase was extracted with ethylacetate (3×30 ml)
  6. dry with materialthe combined organic phases was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-e691220b50314d198373a2da1794aa77
Source dataset
uspto-grants-2010_12
Patent number
US07851629B2

Reaction notes

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