Diethyl Ether → HCID 11781172, compound

HRID 842133Notes

Reaction equation

HRID 842133 reaction equation
[C:1]1([CH:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2].C(OCC)C>C1COCC1.O>[C:1]1([CH:7]([CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:8][NH2:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2191442,3,3-triphenylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 11781172HCID 11781172, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,3,3-triphenylpropionitrile (10.00 g, 0.035 mol) and THF (80 ml) was added dropwise to a solution of LiAlH4 (3.40 g, 0.089 mol) in THF (100 ml) at 0° C. The resulting mixture was stirred for 24 hours at room temperature and then refluxed for 24 hours. After cooling in an ice bath, the reaction mixture was treated with water (3.40 ml), 3N sodium hydroxide (10.20 ml) and water (3.4 ml) followed by the addition of magnesium sulfate. The mixture was filtered and the filtrate was evaporated to an oil. This material was dissolved in diethyl ether (30 ml) and diethyl ether/anhydrous hydrochloric acid (25 ml, 0.025 mol) was added. A white solid was filtered and partitioned between diethyl ether and 3N sodium hydroxide. The organic layer was separated, dried over potassium carbonate, filtered, and evaporated affording 2,3,3-Triphenylpropylamine as a crystalline solid.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureAfter cooling in an ice bath
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to an oil
  5. dissolutionThis material was dissolved in diethyl ether (30 ml)
  6. filtrationA white solid was filtered
  7. custompartitioned between diethyl ether and 3N sodium hydroxide
  8. customThe organic layer was separated
  9. dry with materialdried over potassium carbonate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-983675efbbcd427f85895ecb9cc1a456
Source dataset
uspto-grants-2002_04
Patent number
US06372779B1

Reaction notes

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