Benzaldehyde → HCID 10364246, compound

HRID 914978Notes

Reaction equation

HRID 914978 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH:7]=1.[CH:25]1[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1.[BH4-].[Na+].[OH-].[Na+]>CCO.[Cl-].[Na+].O>[CH2:31]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:23])[CH:14]=2)[CH:7]=1)[C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58958050HCID 58958050, compound

Product 1

HCID 10364246HCID 10364246, compoundYield 456.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of amine 50 (0.22 g, 0.68 mmol) and benzyaldehyde (0.07 mL, 0.08 mmol) in EtOH (3.0 mL) was heated at reflux overnight before it was allowed to cool to room temperature. Sodium borohydride (0.04 g, 0.80 mmol) was added and the reaction was stirred at room temperature for 1 hour. The mixture was mixed with 2N NaOH (3.0 mL), brine (2.0 mL), and extracted with 7:3 CH2Cl2/MeOH (3×5.0 mL). The combined organic layers were dried (K2CO3) and concentrated under reduced pressure. The residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH) to yield the desired product (0.15 g, 62%) as a pale yellow solid.

Workup

  1. temperatureat reflux overnight before it
  2. extractionextracted with 7:3 CH2Cl2/MeOH (3×5.0 mL)
  3. dry with materialThe combined organic layers were dried (K2CO3)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatrography (SiO2, gradient elution, 3:1 hexanes/EtOAc to 7:3 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-34f64baf5b584fb98b7545bf945218ca
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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