Toluene → 2-(Phenoxymethyl)piperidine

HRID 2186480Notes

Reaction equation

HRID 2186480 reaction equation
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.CCOC(C)=O>C(O)(=O)C.C(Cl)Cl.[Pt]>[O:1]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 22456677HCID 22456677, compound

Product 1

HCID 224566822-(Phenoxymethyl)piperidine

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenoxymethylpyridine (1.0 g, 5.4 mmol) in 23 mL of acetic acid was added 0.13 g of 5% Pt/C. The mixture was hydrogenated on a Parr shaker at 50 psi for 5 h. Toluene and EtOAc were added to the mixture and it was filtered and concentrated under reduced pressure to give an oil. The oil was dissolved in CH2Cl2 and washed with 10% NaOH. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give a 50/50 mixture of the title compound and starting material as a yellow oil (1.0 g, 98%). ES (+) MS m/e=192 (M+H).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated under reduced pressure
  3. customto give an oil
  4. washwashed with 10% NaOH
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give

Sources & evidence

ORD record
ord-2dfd1e9386d64d5a8abf7a5c3e19bb1c
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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