Hydrochloric Acid → 2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethanaminium chloride

HRID 1943019Notes

Reaction equation

HRID 1943019 reaction equation
[C:1]1([C:7](=[C:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:16]>C(O)C.[Pd]>[Cl-:16].[C:1]1([CH:7]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:8][NH3+:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58415944phenyl(tetrahydro-4H-pyran-4-ylidene)acetonitrile

Product 1

HCID 673936932-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethanaminium chloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To phenyl(tetrahydro-4H-pyran-4-ylidene)acetonitrile (450 mg, 2.258 mmol) in ethanol (11 ml) was added HCl (12.1 M, 1.867 ml, 22.58 mmol) then 10% Pd/C (48.1 mg, 0.045 mmol) as a slurry in ethanol. The reaction mixture was put under H2 balloon pressure for 21 hours. The reaction was filtered through a 0.45 um syringe-tip filter, then concentrated in vacuo. The product was used without further purification.

Workup

  1. customfor 21 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-634180e68ae74ad886286a27cf275d30
Source dataset
uspto-grants-2013_03
Patent number
US08389720B2

Reaction notes

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