Water → N-[1-(Aminomethyl)cyclohexyl]aniline

HRID 1894850Notes

Reaction equation

HRID 1894850 reaction equation
[C:1]1([NH:7][C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[NH2:15][CH2:14][C:8]1([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2910301-Phenylamino-cyclohexanecarbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 16227755N-[1-(Aminomethyl)cyclohexyl]anilineYield 39.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5 g (25 mmol) of 1-phenylaminocyclohexanecarbonitrile in 70 ml of ethyl ether is added drop by drop to 1.13 g (29.8 mmol) of lithium aluminum hydride in 30 ml of ethyl ether at 0° C. The mixture is stirred for 2 hours at 0° C. The reaction is stopped by the addition of 1.1 ml of water, 1.1 ml of 15% sodium hydroxide and then 3.5 ml of water. The medium is then filtered on Celite and the filtrate is evaporated. The residue is purified on silica gel (dichloromethane then dichloromethane/methanol 80/20, v/v). 2 g of (1-aminomethylcyclohexyl)phenylamine are obtained in the form of a brown oil. Yield=39%.

Workup

  1. filtrationThe medium is then filtered on Celite
  2. customthe filtrate is evaporated
  3. customThe residue is purified on silica gel (dichloromethane

Sources & evidence

ORD record
ord-0fe370108a194e3bac8bab05f99e79cd
Source dataset
uspto-grants-2013_08
Patent number
US08513307B2

Reaction notes

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