Formic Acid → HCID 59815626, compound

HRID 2241905Notes

Reaction equation

HRID 2241905 reaction equation
C=O.[CH:3](O)=O.[F:6][C:7]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.C(=O)([O-])O.[Na+]>O>[F:6][C:7]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH3:3])[CH2:12]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 59205046HCID 59205046, compound

Product 1

HCID 59815626HCID 59815626, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

38% aqueous formaldehyde (1.00 ml) and formic acid (1.00 ml) were added to 3-(2-fluoro-4-nitrophenoxymethyl)piperidine (compound of Reference Example 53; 0.300 g, 1.18 mmol), and the mixture was stirred at 90° C. for 1 hour. The reaction mixture was adjusted to pH=8 by addition of saturated aqueous sodium hydrogencarbonate, diluted with water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel to give the title compound (0.275 g, 87%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customThe residue obtained by evaporation of the solvent under reduced pressure
  4. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0241c30df89d47a084258d4d0cdc0099
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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