4-Fluorobenzylamine → HCID 178522995, compound

HRID 2267101Notes

Reaction equation

HRID 2267101 reaction equation
CO[C:3](=[O:21])[C:4]1[C:9]([OH:10])=[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]([CH2:19][OH:20])=[N:6][CH:5]=1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1>CN(C)C=O>[CH2:12]([O:11][C:8]1[C:7]([CH2:19][OH:20])=[N:6][CH:5]=[C:4]([C:9]=1[OH:10])[C:3]([NH:28][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([F:22])=[CH:24][CH:25]=1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 178498811HCID 178498811, compound

Product 1

HCID 178522995HCID 178522995, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The compound 18 (3.76 g, 13.0 mmol) was dissolved in dimethylformamide (38 ml), and 4-fluorobenzylamine (2.44 ml, 21.3 mmol) was added, followed by stirring at 120° C. for 2 hours. The reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure, followed by dilution with ethyl acetate. Thereafter, this was washed with 2N hydrochloric acid and water, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with diethyl ether to obtain 5-benzyloxy-N-(4-fluoro-benzyl)-4-hydroxy-6-hydroxymethyl-nicotinic acid amide 10 (3.59 g, 72%) as a beige crystal.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. washThereafter, this was washed with 2N hydrochloric acid and water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-95a7cf67cbe94d8b89567f3b5d403bc3
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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