Ethanolamine → HCID 33788885, compound

HRID 1019736Notes

Reaction equation

HRID 1019736 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[F:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH:8]=O.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO.C(Cl)Cl>[F:5][C:6]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:7]=1[CH2:8][NH:4][CH2:3][CH2:1][OH:2]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 737702,4-DifluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 33788885HCID 33788885, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethanolamine (0.86 g, 14.07 mmol) was added to a solution of 2,4-difluorobenzaldehyde (2.0 g, 14.07 mmol) in methanol (50 mL) at RT. Sodium bicarbonate (7.0 g, 83.33 mmol) was added and the reaction mixture was stirred at reflux for 24 hours. The mixture was cooled to 0° C. and sodium borohydride (0.32 g, 8.42 mmol) was then added in lots, maintaining the temperature of the mixture at 0-5° C. The reaction mixture was allowed to warm to RT over a period of 4 hours. The reaction mixture was then diluted with DCM (50 mL), washed with brine (2×30 mL), dried (Na2SO4) and the solvents removed under reduced pressure to afford the title compound (1.79 g, 69%). The product was used in the next step without further purification.

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturemaintaining the temperature of the mixture at 0-5° C
  3. temperatureto warm to RT over a period of 4 hours
  4. washwashed with brine (2×30 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-f1c9c72b40d843b3ba71edba9d6e18e9
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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