Benzaldehyde → HCID 66975653, compound

HRID 1022641Notes

Reaction equation

HRID 1022641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]2)[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH2:19]([NH:11][CH2:10][CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 66975729HCID 66975729, compound

Product 1

HCID 66975653HCID 66975653, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2RS)-2-(3,4-dichlorophenyl)-2-[(4RS)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanamine (10.1 g) in toluene (200 mL) was added benzaldehyde (4.43 g) at room temperature. The mixture was heated under reflux for 1 hr while dehydrating by a Dean-Stark trap, cooled to room temperature, and concentrated under reduced pressure. To the residue was added methanol (60 ml), sodium tetrahydroborate (658 mg) was added under ice-cooling, and the mixture was stirred for 1 hr. The reaction was quenched with water, methanol was evaporated under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (5%-100%)) to give the title compound (7.96 g) as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added methanol (60 ml), sodium tetrahydroborate (658 mg)
  5. additionwas added under ice-
  6. temperaturecooling
  7. customThe reaction was quenched with water, methanol
  8. customwas evaporated under reduced pressure
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent was evaporated
  13. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (5%-100%))

Sources & evidence

ORD record
ord-c286c45d1028482686d99cfffe2d894a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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