Water → HCID 15662564, compound

HRID 1073428Notes

Reaction equation

HRID 1073428 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH:11]([CH3:14])[C:12]#[N:13])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:17][C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH:11]([CH3:14])[CH2:12][NH2:13])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15662563HCID 15662563, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15662564HCID 15662564, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 2-[4-(3-methyl-2-butenoxy)phenoxy]propionitrile (2.0 g, 8.6 mmol) in 20 ml of ether is added lithium aluminum hydride (0.328 g, 8.6 mmol) in portions at 5°. After the addition, the reaction mixture is slowly warmed to RT and stirred for 18 hours. The reaction is worked up by cooling to 5° and by adding 0.33 ml of water, followed by 0.33 ml of 15% NaOH and 1 ml of water, with vigorous stirring. The solid is filtered off and the filtrate is washed with brine and dried over calcium sulfate. The ether is removed to give 2-[4-(3-methyl-2-butenoxy)phenoxy]propylamine.

Workup

  1. additionAfter the addition
  2. temperatureby cooling to 5°
  3. filtrationThe solid is filtered off
  4. washthe filtrate is washed with brine
  5. dry with materialdried over calcium sulfate
  6. customThe ether is removed

Sources & evidence

ORD record
ord-d5ce15a923914878beba3136dcd93c22
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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