Water → 2-(4-Benzylphenoxy)ethanamine

HRID 2254560Notes

Reaction equation

HRID 2254560 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][C:20]#[N:21])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:7]([C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][NH2:21])=[CH:22][CH:23]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19742794(4-Benzylphenoxy)acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 106093492-(4-Benzylphenoxy)ethanamineYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.4 g of lithium aluminum hydride was suspended in 100 ml of anhydrous tetrahydrofuran and to the suspension was gradually added 10.0 g of (4-benzylphenoxy)acetonitrile under ice cooling in nitrogen stream. After stirring at room temperature for 1 hour and ice cooling, to the reaction mixture were carefully added 3.4 ml of water, then 3.4 ml of 5N aqueous sodium hydroxide solution and finally 10 ml of water, followed by stirring for a while. Undesired matters were removed by filtration with cerite and the filtrate was concentrated under reduced pressure to obtain 9.8 g of 2-(4-benzylphenoxy)ethylamine. This was used for the subsequent reaction without further purification.

Workup

  1. stirringby stirring for a while
  2. customUndesired matters were removed by filtration with cerite and the filtrate
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa23549eeb29406fabb482d6d6705b79
Source dataset
uspto-grants-1993_08
Patent number
US05236924

Reaction notes

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