Sodium Sulfate → HCID 69749576, compound

HRID 1882768Notes

Reaction equation

HRID 1882768 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[C:12]#[N:13])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:1]1([CH:7]([NH:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]=2[CH2:12][NH2:13])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 69749319HCID 69749319, compound

Product 1

HCID 69749576HCID 69749576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 3a above, (+/−)-2-[(1-phenyl)ethylamino]-6-phenybenzonitrile, (0.13 g, 0.43 mmol) was dissolved in dry tetrahydrofuran (10 mL) and stirred under argon at room temperature. Lithium aluminum hydride (0.172 g, 4.3 mmol) was added and the mixture heated to reflux under argon for 20 hours. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate. The solvent was evaporated and the residue triturated with ethyl acetate, filtered and evaporated. Flash chromatography on silica gel eluted with 0-3% methanol in methylene chloride followed by recrystallization from ethyl acetate/hexane gave the title compound as a white crystalline solid. ES (+) MS n/e=303 (MH+)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux under argon for 20 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe solvent was evaporated
  5. customthe residue triturated with ethyl acetate
  6. filtrationfiltered
  7. customevaporated
  8. washFlash chromatography on silica gel eluted with 0-3% methanol in methylene chloride
  9. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7c4971be53a0476e83bc63ddf97acf6b
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

Loading…