Diethyl Ether → Ifoxetine

HRID 1046523Notes

Reaction equation

HRID 1046523 reaction equation
[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7][C@H:6]1[OH:21].[H][H].C(OCC)C>CO.[Pd]>[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][NH:8][CH2:7][C@H:6]1[OH:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 68898008cis-Benzyl 4-(2,3-dimethylphenoxy)-3-hydroxypiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 71971IfoxetineYield 67.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of cis-benzyl 4-(2,3-dimethylphenoxy)-3-hydroxypiperidine-1-carboxylate (5.0 g, 14.0 mmol) in methanol (60 ml) was added to 5% palladium on charcoal (500 mg) under an atmosphere of nitrogen. The vessel was placed under an atmosphere of hydrogen and stirred vigorously until hydrogen uptake ceased. The resulting suspension was filtered over a short pad of celite (pre-washed with methanol) and the pad washed with a further portion of methanol (150 ml). Concentration of the methanolic solution in vacuo gave a yellow oil. Dilution with diethyl ether (150 ml) yielded cis-4-(2,3-dimethylphenoxy)-3-hydroxypiperidine as a white solid (2.1 g, 67%).

Workup

  1. filtrationThe resulting suspension was filtered over a short pad of celite (pre-washed with methanol)
  2. washthe pad washed with a further portion of methanol (150 ml)
  3. customConcentration of the methanolic solution in vacuo gave a yellow oil

Sources & evidence

ORD record
ord-7c77d44ec8e84e52abb4ca8bdac9ad8d
Source dataset
uspto-grants-2013_10
Patent number
US08569342B2

Reaction notes

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