Sodium Hydroxide → HCID 15027460, compound

HRID 1196035Notes

Reaction equation

HRID 1196035 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:11]([CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:15]1)#[N:12].[OH-].[Na+]>C(OCC)C.O1CCCC1.O>[NH2:12][CH2:11][CH2:13][CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[O:15]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 148384413,4-Dihydro-2H-1-benzopyran-2-acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 15027460HCID 15027460, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

First, at room temperature and while stirring, 2.2 g (16.5 mmol) of aluminium chloride in 70 ml of absolute diethyl ether are added dropwise to a suspension of 3.8 g (100 mmol) of lithium aluminium hydride in 150 ml of absolute diethyl ether. Then 8.66 g (50 mmol) of 2-cyanomethylchroman in 70 ml of absolute tetrahydrofuran are added dropwise within a period of 20 minutes. The reaction mixture is stirred for a further 16 hours at room temperature and then carefully decomposed with 3.8 ml of water, 3.8 ml of sodium hydroxide solution (15% strength) and 11.4 ml of water. The precipitate formed is filtered off with suction and the filtrate is concentrated by evaporation in vacuo. The oily residue is dissolved in diethyl ether. The ethereal phase is washed with water, dried over sodium sulphate and concentrated by evaporation. 8.75 g (98.8%) of 2-(2-aminoethyl)chroman are obtained in the form of a colourless oil.

Workup

  1. stirringThe reaction mixture is stirred for a further 16 hours at room temperature
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. dissolutionThe oily residue is dissolved in diethyl ether
  6. washThe ethereal phase is washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a98d6675681841588830aa5a37383f3e
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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