Sodium Hydroxide → (4-Benzylmorpholin-2-yl)methanamine

HRID 1608207Notes

Reaction equation

HRID 1608207 reaction equation
[N:1]([CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=[N+]=[N-].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:1][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19848617HCID 19848617, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 2776360(4-Benzylmorpholin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 2-azidomethyl-4-benzylmorpholine (15 g) in toluene (40 ml) is added dropwise to a stirred solution of 70% sodium bis(2-methoxyethoxy)aluminum hydride in toluene (60 ml) cooled to -5° C. The reaction mixture is stirred at 25° C. for 1.5 hours and cooled to 10° C., and the excess of the reducing agent is decomposed by the cautious addition of 10% aqueous sodium hydroxide solution. The organic layer is separated, washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. After removal of the solvent under reduced pressure, the title compound is obtained a an oil (11 g).

Workup

  1. temperaturecooled to 10° C.
  2. customThe organic layer is separated
  3. washwashed successively with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0c0bb2662aa644fabf6869b577f682b0
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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