5-(Dimethylamino)pentanenitrile → 5-(Dimethylamino)amylamine

HRID 1264297Notes

Reaction equation

HRID 1264297 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14]>CCOCC>[CH3:7][N:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 53056495-(Dimethylamino)pentanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 34659255-(Dimethylamino)amylamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of lithium aluminum hydride (8 ml, 0.5M in ether) is added, slowly, a solution of 5-(dimethylamino)-pentanenitrile (126 mg, 1 mmol, reference example 94a) in ether (1 mL). On complete addition, the cold bath is removed and stirring continued for 2 h. The reaction mixture is then cooled to 0° C. and quenched by dropwise addition of water (160 mL), sodium hydroxide solution (160 mL, 5M), then a further portion of water (160 mL). The resulting mixture is filtered through celite and the filtrate concentrated under reduced pressure to give an oil which is used without further purification.

Workup

  1. additionis added
  2. additionOn complete addition
  3. customthe cold bath is removed
  4. customquenched by dropwise addition of water (160 mL), sodium hydroxide solution (160 mL, 5M)
  5. filtrationThe resulting mixture is filtered through celite
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto give an oil which
  8. customis used without further purification

Sources & evidence

ORD record
ord-2fc9aaaf4972498191a4e8b350251896
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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