Water → N-Benzylputrescine

HRID 1493887Notes

Reaction equation

HRID 1493887 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)#[N:8].O.[OH-].[Na+]>O1CCCC1>[CH2:13]([NH:12][CH2:11][CH2:10][CH2:9][CH2:7][NH2:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 30145704-(Benzylamino)butanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 152999N-BenzylputrescineYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.1 g of lithium aluminum hydride in 50 ml of tetrahydrofuran was added slowly 2.9 g of N-(3-cyanopropyl)benzylamine (obtained in Reference Example 4) at room temperature. The reaction mixture was heated gently under reflux for 15 minutes and then allowed to cool. To the mixture was added dropwise and carefully 2.2 ml of water and then 1.8 ml of 10% aqueous sodium hydroxide. The resultant precipitate was filtered off, the filtrate was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give 1.7 g of N-benzyl-1,4-butanediamine as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated gently
  2. temperatureunder reflux for 15 minutes
  3. temperatureto cool
  4. additionTo the mixture was added dropwise
  5. filtrationThe resultant precipitate was filtered off
  6. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d583353b775646039a92d8465ca5e4ec
Source dataset
uspto-grants-1991_06
Patent number
US05025033

Reaction notes

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