Sodium sulfate decahydrate → 1-(4-Methoxyoxan-4-yl)methanamine

HRID 1297335Notes

Reaction equation

HRID 1297335 reaction equation
[C:1]([C:3]1([O:9][CH3:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH3:10][O:9][C:3]1([CH2:1][NH2:2])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 218090184-Methoxyoxane-4-carbonitrile

Product 1

HCID 552850801-(4-Methoxyoxan-4-yl)methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under ice-cooling, a diethyl ether (5 ml) solution of 4-cyano-4-methoxytetrahydropyran (600 mg; Chemistry Letters, pp. 937-940, 1984) was added dropwise to a diethyl ether (10 ml) suspension of lithium aluminum hydride (242 mg) spending 20 minutes and, after completion of the dropwise addition, stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was ice-cooled, and sodium sulfate decahydrate was gradually added to the reaction mixture until foaming stopped. After completion of the addition, the insoluble matter was filtered, and the filtered solid was washed with diethyl ether. The filtrate and washed solution were combined and concentrated under a reduced pressure to obtain the title compound (597 mg).

Workup

  1. temperatureUnder ice-cooling
  2. additionafter completion of the dropwise addition
  3. customAfter completion of the reaction
  4. temperaturecooled
  5. additionAfter completion of the addition
  6. filtrationthe insoluble matter was filtered
  7. washthe filtered solid was washed with diethyl ether
  8. washThe filtrate and washed solution
  9. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-19bc2c69baed445a9e3426e039f7bbbf
Source dataset
uspto-grants-2007_07
Patent number
US07250429B2

Reaction notes

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