Water → (4-Aminomethylphenyl)-benzylamine

HRID 2079984Notes

Reaction equation

HRID 2079984 reaction equation
[CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1)[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>[NH2:14][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 99425094-(Benzylamino)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 23130504(4-Aminomethylphenyl)-benzylamineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzylamino-benzonitrile (472 mg, 2.27 mmol) described in Preparation Example 89 was dissolved at 0° C. in tetrahydrofuran (20 mL), and lithium aluminum hydride (430 mg, 11.3 mmol) was added thereto. The solution was stirred overnight at room temperature, then, at 0° C., water (430 μl ), an aqueous solution of 5N sodium hydroxide (430 μl ) and water (1.29 mL) were sequentially added to the solution. The reaction solution was filtered through Celite pad, the solvent was then evaporated in vacuo, (4-aminomethyl-phenyl)-benzylamine (475 mg, 2.24 mmol, 99%) was obtained as an oil.

Workup

  1. filtrationThe reaction solution was filtered through Celite pad
  2. customthe solvent was then evaporated in vacuo

Sources & evidence

ORD record
ord-af11d89a6679456592ddb2b39996bb31
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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