Trimethyl orthoformate → 3-Fluoro-1-(2-fluoro-4-nitrophenyl)-4,4-dimethoxypiperidine

HRID 750907Notes

Reaction equation

HRID 750907 reaction equation
[F:1][CH:2]1C(=O)[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH2:3]1.[CH3:19][O:20][CH:21](OC)[O:22][CH3:23].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:19][O:20][C:21]1([O:22][CH3:23])[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH2:3][CH:2]1[F:1]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 597540583-Fluoro-1-(2-fluoro-4-nitrophenyl)piperidin-4-one

Product 1

HCID 597540593-Fluoro-1-(2-fluoro-4-nitrophenyl)-4,4-dimethoxypiperidineYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

The mixture of 4-(3-fluoro-4-oxo-piperidin-1-yl)-3-fluoronitrobenzene (65 mmol), trimethylorthoformate (130 mmol), p-toluene-sulphonic acid monohydrate (67 mmol) in methanol was heated at 45° C. for 24 hours. Solvent was removed and residual mass was taken into ethyl acetate and saturated sodium bicarbonate solution mixture. The organic layer was dried and removal of the solvent afforded title compound as a solid in 78% yield.

Workup

  1. customSolvent was removed
  2. customThe organic layer was dried
  3. customremoval of the solvent

Sources & evidence

ORD record
ord-9381e4ea2cc94baca4866eeed68574ed
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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