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

HRID 1081199Notes

Reaction equation

HRID 1081199 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-bf43a01aad64413bb2e299c8aab486c4
Source dataset
uspto-grants-1996_12
Patent number
US05583133

Reaction notes

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