Hydrochloric Acid → 2-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-phenylethanaminium chloride

HRID 1943022Notes

Reaction equation

HRID 1943022 reaction equation
[OH:1][C:2]1([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[ClH:17]>C(O)C.[Pd]>[Cl-:17].[OH:1][C:2]1([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][NH3+:10])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58415919(4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile

Product 1

HCID 673940692-(4-hydroxytetrahydro-2H-pyran-4-yl)-2-phenylethanaminium chloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To (4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile (50 mg, 0.230 mmol) in ethanol (2 ml) was added HCl (0.190 ml, 2.301 mmol) then 10% Pd/C (49.0 mg, 0.046 mmol) as a slurry in ethanol. The reaction mixture was put under H2 balloon pressure for 15 hours. The reaction was filtered through a 0.45 um syringe-tip filter, then concentrated in vacuo. The product was used without further purification. 49.6 mg, 84%.

Workup

  1. customfor 15 hours
  2. filtrationThe reaction was filtered through a 0.45 um syringe-tip
  3. filtrationfilter
  4. concentrationconcentrated in vacuo
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-98ccbd1792d24d61946dc275557a911e
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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