Benzylethanolamine → HCID 66618867, compound

HRID 406368Notes

Reaction equation

HRID 406368 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.S(=O)(O)[O-].[Na+].[C-:18]#[N:19].[Na+].[CH2:21]([NH:28][CH2:29][CH2:30][OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.CO>[CH2:21]([N:28]([CH:7]([C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1)[C:18]#[N:19])[CH2:29][CH2:30][OH:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 4348BenzylethanolamineHCID 8929Sodium CyanideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 66618867HCID 66618867, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

4-(Trifluoromethyl)benzaldehyde (CAS #455-19-6, 2 g) and methanol (1 mL) were added to a solution of sodium bisulfite (1.33 g) in water (40 mL) at room temperature, and the mixture was stirred at room temperature for 10 minutes. Sodium cyanide (1.33 g) was added to the reaction solution, and the mixture was stirred at the same temperature for 40 minutes. N-Benzylethanolamine (1.83 g) and methanol (3 mL) were added to the reaction solution, and the mixture was stirred at the same temperature for 16 hours. The reaction solution was partitioned with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1) to obtain 1.79 g of the title compound. The property values of the compound are as follows.

Workup

  1. stirringthe mixture was stirred at the same temperature for 40 minutes
  2. stirringthe mixture was stirred at the same temperature for 16 hours
  3. customThe reaction solution was partitioned with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-a9fdb9b86cbf43e2815ac6d1d2d667c2
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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