Sodium Hydroxide → 2-((Benzyloxy)methyl)morpholine

HRID 257278

Reaction equation

HRID 257278 reaction equation
S(O)([O:4][CH2:5][CH2:6][NH2:7])(=O)=O.[OH-].[Na+].[CH2:11]([O:18][CH2:19][CH:20]1[CH2:22]O1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH2:11]([O:18][CH2:19][CH:20]1[O:4][CH2:5][CH2:6][NH:7][CH2:22]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 70223Aminoethyl sulfateHCID 94247Benzyl glycidyl ether

Product 1

HCID 136700222-((Benzyloxy)methyl)morpholine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

199 g of 2-aminoethyl hydrogen sulfate are added to 164 ml of 70% sodium hydroxide solution, the solution is heated to 50° C. and added dropwise to a solution of (RS)-benzyloxymethyloxirane in 280 ml of methanol. After 1 hour at 50° C. a further 280 ml of 70% sodium hydroxide solution are added thereto and the solution is stirred overnight. Then, the reaction mixture is poured on to ice and extracted with toluene. The organic phase is washed with water, dried and evaporated. After distillation there are obtained 26.8 g of rac-2-benzyloxymethylmorpholine, MS: M+ -91=116 (benzyl).

Workup

  1. additionThen, the reaction mixture is poured on to ice
  2. extractionextracted with toluene
  3. washThe organic phase is washed with water
  4. customdried
  5. customevaporated
  6. distillationAfter distillation

Sources & evidence

ORD record
ord-1e506a4d26304ae08c89fe3fcd0bbae1
Source dataset
uspto-grants-1993_11
Patent number
US05260307

Linked notes

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