Trimethyl orthoformate → 3-Fluoro-4,4-dimethoxy-1-(4-nitrophenyl)piperidine

HRID 750898Notes

Reaction equation

HRID 750898 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][CH:10]=2)[CH2:3]1.[CH3:18][O:19][CH:20](OC)[O:21][CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:18][O:19][C:20]1([O:21][CH3:22])[CH2:6][CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:3][CH:2]1[F:1]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 597541273-Fluoro-1-(4-nitrophenyl)piperidin-4-one

Product 1

HCID 597539773-Fluoro-4,4-dimethoxy-1-(4-nitrophenyl)piperidineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

The mixture of 4-(3-fluoro-4-oxo-piperidin-1-yl)-nitrobenzene (51 mmol), trimethylorthoformate (103 mmol), p-toluene-sulphonic acid monohydrate (51 mmol) in methanol (100 ml) 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 91% yield.

Workup

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

Sources & evidence

ORD record
ord-72123f4c54c9474889dd80e6cb7548f3
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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