Water → 4-(2-Methyl-butyl)-benzylamine

HRID 911659Notes

Reaction equation

HRID 911659 reaction equation
CS(O[CH:6]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH:7]([CH3:10])[CH2:8][CH3:9])(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:10][CH:7]([CH2:8][CH3:9])[CH2:6][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 576560524-(1-Methanesulfonyloxy-2-methyl-butyl)-benzonitrile

Product 1

HCID 576561404-(2-Methyl-butyl)-benzylamineYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, add a mixture of 4-(1-methanesulfonyloxy-2-methyl-butyl)-benzonitrile (1.3 g, 4.9 mmol) in diethyl ether (5 mL) to a slurry of lithium aluminum hydride (820 mg, 19.5 mmol) in diethyl ether (25 mL) at 0° C. Heat the mixture under reflux for 1 h. Cool the mixture in an ice-bath and add water (0.9 mL), 15% aqueous NaOH (0.9 mL) and water (2.8 mL). Apply the mixture to a silica gel column eluting with dichloromethane and 5:1 dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2) to provide the title compound (450 mg, 52%). MS (ES+) m/z: 178 (M+H)+.

Workup

  1. additionUnder a nitrogen atmosphere, add
  2. temperatureHeat the mixture
  3. temperatureunder reflux for 1 h
  4. temperatureCool the mixture in an ice-bath
  5. washApply the mixture to a silica gel column eluting with dichloromethane and 5:1 dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2)

Sources & evidence

ORD record
ord-0537b15730634950833d966e61c032f8
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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