Water → N~1~-Benzyl-N~1~-tert-butylethane-1,2-diamine

HRID 1893507Notes

Reaction equation

HRID 1893507 reaction equation
[CH2:1]([N:8]([CH2:13][C:14]#[N:15])[C:9]([CH3:12])([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:13][CH2:14][NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11790275Acetonitrile, [(1,1-dimethylethyl)(phenylmethyl)amino]-HCID 21226445Aluminium lithium hydride

Product 1

HCID 12861881N~1~-Benzyl-N~1~-tert-butylethane-1,2-diamineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (5.00 g, 24.7 mmol) obtained in step A was dissolved in tetrahydrofuran (100 ml), and the mixture was stirred under ice-cooling. Lithium aluminum hydride (1.87 g, 49.4 mmol) was gradually added at the same temperature, and the mixture was stirred at room temperature for 2 hr. After ice-cooling again, water (1.9 ml), 1N aqueous sodium hydroxide solution (3.8 ml) and water (1.9 ml) were gradually added in this order, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off through celite, and the obtained solution was concentrated under reduced pressure to give the title compound (4.89 g, yield 96%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. temperatureAfter ice-cooling again
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. filtrationThe insoluble material was filtered off through celite
  6. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7cf64d5e214b405ea5f3f048e31b06be
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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