Water → HCID 19351116, compound

HRID 1636381Notes

Reaction equation

HRID 1636381 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([NH2:18])=O)[CH:10]=[CH:9]2)=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([N:3]([CH2:4][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16][NH2:18])[CH:10]=[CH:9]2)[CH2:19][CH3:20])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19351171HCID 19351171, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19351116HCID 19351116, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-(diethylaminocarbonyl)-2-naphthalenecarboxamide (11.6 g, 42 mmol) in THF (100 ml) was slowly added to a refluxing suspension of lithium aluminium hydride (4.9 g, 128 mmol) in THF (100 ml). The mixture was refluxed for 2 hours, then cooled at room temperature and treated with a mixture of THF (16 ml) and water (2.2 ml), with 20% sodium hydroxide (5.5 ml) and finally with water (22 ml). The white solid was filtered off and the solvent was removed under reduced pressure. Crude was purified by chromatography on silica gel (eluent chloroform-methanol-ammonium hydroxide 15:1:0.1) yielding 8.1 g (Yield 80%) of pure 6-(diethylaminomethyl)-2-naphthylmethylamine as waxy solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. filtrationThe white solid was filtered off
  3. customthe solvent was removed under reduced pressure
  4. customCrude was purified by chromatography on silica gel (eluent chloroform-methanol-ammonium hydroxide 15:1:0.1)

Sources & evidence

ORD record
ord-4e83ec29d8e74581b6457b8dd721ea7b
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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