Benzaldehyde → HCID 91488052, compound

HRID 584774Notes

Reaction equation

HRID 584774 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:15])[CH:11]=[C:12]([CH3:14])[CH3:13].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].[OH-].[Na+]>CO.C(OCC)(=O)C>[CH2:16]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:15])[CH:11]=[C:12]([CH3:13])[CH3:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20821695HCID 20821695, compound

Product 1

HCID 91488052HCID 91488052, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

The product of Example 1 (612 mg, 3.0 mmol) was placed in a 25 mL round bottom flask and dissolved in methanol (6 mL). To this solution was added benzaldehyde (0.32 mL, 3.0 mmol) and the mixture was stirred at room temperature for 1 hr. After this time sodium borohydride (170 mg, 4.5 mmol) was added slowly over 10 minutes, and the mixture was allowed to stir for an additional 20 minutes. 15 mL of 1N NaOH was then added to quench the reaction, and the mixture was transferred to a separatory funnel with ethyl acetate. An additional 25 mL of ethyl acetate was added and the organic layer was washed successively with 1N NaOH (3×15 mL), brine (1×15 mL), and then dried over magnesium sulfate, filtered, and evaporated. The product was purified by flash column chromatography with ethyl acetate-hexane (3:7 then 1:1) to yield 3-methyl-but-2-enoic acid [2-(benzylamino-methyl)-phenyl]-amide (839 mg, 95% yield) of a yellow oil. 1H NMR (250 MHz, CDCl3) 10.44 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.39-6.84 (m, 8H), 5.64-5.56 (m, 1H), 3.78 (s, 2H), 3.70 (s, 2H), 2.15 (s, 3H), 1.82 (s, 3H). The amine was then converted to the HCl salt with an excess of 1N HCl in ether to be used in further transformations.

Workup

  1. stirringto stir for an additional 20 minutes
  2. customto quench
  3. customthe reaction
  4. washthe organic layer was washed successively with 1N NaOH (3×15 mL), brine (1×15 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified by flash column chromatography with ethyl acetate-hexane (3:7

Sources & evidence

ORD record
ord-d38a6429fb7248f1b10795af70b5e865
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

Loading…