4-[2-(Diethylamino)ethoxy]benzonitrile → {4-[2-(Diethylamino)ethoxy]phenyl}methanamine

HRID 1858220Notes

Reaction equation

HRID 1858220 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH2:21][CH3:22])[CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)[CH3:8]>O1CCCC1>[CH2:21]([N:9]([CH2:7][CH3:8])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][NH2:18])=[CH:19][CH:20]=1)[CH3:22]

Participants

4

Reactant 2

HCID 3410044-[2-(Diethylamino)ethoxy]benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 235944{4-[2-(Diethylamino)ethoxy]phenyl}methanamineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of lithium aluminium hydride (5 ml; 5 mmol) was added dropwise to a stirred solution of 1.01 g (5 mmol) of 4-(2-diethylaminoethoxy)benzonitrile in 5 ml of dry tetrahydrofuran at 0° C. The mixture was warmed to room temperature and stirred overnight. The reaction was quenched by the cautious addition of a saturated solution of 5 ml of Rochelle's salt and then evaporated. The residue was partitioned between 25 ml of diethyl ether and 25 ml of water and the organic phase was separated, dried over magnesium sulfate and evaporated. The crude product was purified by flash column chromatography on silica gel using dichloromethane/methanol/water/acetic acid (60:18:2:3) for the elution. Product-containing fractions were combined and evaporated to give 785 mg (71%) of 4-(2-diethylaminoethoxy)benzylamine as a colorless oil. [Mass spectrum (ESI) MH+ =223].

Workup

  1. customThe reaction was quenched by the cautious addition of a saturated solution of 5 ml of Rochelle's salt
  2. customevaporated
  3. customThe residue was partitioned between 25 ml of diethyl ether and 25 ml of water
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography on silica gel
  8. washfor the elution
  9. customevaporated

Sources & evidence

ORD record
ord-b46d2b8fa45345d09c96ddb8a2290ac2
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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