Sodium borohydride → HCID 19744522, compound

HRID 2254417Notes

Reaction equation

HRID 2254417 reaction equation
[CH2:1]([N:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([O:12][CH3:13])([CH3:11])[CH3:10])[CH3:2].[S:22]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[CH:30]=O)=[CH:23]1.[BH4-].[Na+].C(Cl)Cl.CO>CO>[CH2:1]([N:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[C:27]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)[CH:28]=2)[CH:16]=1)[CH2:4]/[CH:5]=[CH:6]/[C:7]#[C:8][C:9]([O:12][CH3:13])([CH3:11])[CH3:10])[CH3:2]

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 45475263-(Thiophen-3-yl)benzaldehydeHCID 19744585HCID 19744585, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 19744522HCID 19744522, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

65 mg of (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-3-aminobenzylamine and 43 mg of 3-(3thienyl)benzaldehyde were dissolved in 2 ml of methanol, and the solution was stirred overnight at room temperature. With stirring under ice cooling, 12.9 mg of sodium borohydride was added, and stirred for 1 hour at room temperature. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate and water. The organic layer was separated, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography Wakogel C-200, 5 g; eluting solvent: methylene chloride/ methanol=60/1] to give 87 mg (yield 84%) of the captioned compound as a pale yellow oil.

Workup

  1. stirringWith stirring under ice cooling
  2. stirringstirred for 1 hour at room temperature
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe desiccant was separated by filtration
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography Wakogel C-200, 5 g

Sources & evidence

ORD record
ord-83df4b4bd28a46fdad9216cdba7c3c28
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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