(4-Benzylmorpholin-2-yl)methanamine → (S)-(4-benzylmorpholin-2-yl)methanamine

HRID 324957Notes

Reaction equation

HRID 324957 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1>C(O)C>[NH2:1][CH2:2][C@@H:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1

Participants

3

Reactant 1

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

Product 1

HCID 6932054(S)-(4-benzylmorpholin-2-yl)methanamineYield 42.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(RS)-2-Aminomethyl-4-benzylmorpholine (326.1 g) was dissolved in ethanol (3 L) and dibenzoyl-D-tartaric monohydrate (535 g) was added. The mixture was refluxed for dissolution and then left standing at room temperature for 16 hours. The precipitated crystals were collected by filtration and recrystallized from a mixed solvent of ethanol:water=25:1. The obtained crystals were suspended in water (1.2 L) and aqueous sodium hydroxide solution was added with stirring to make the suspension basic, which was followed by extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled off to give 138.4 g of (S)-2-aminomethyl-4-benzylmorpholine as a colorless oil.

Workup

  1. temperatureThe mixture was refluxed for dissolution
  2. waitleft
  3. filtrationThe precipitated crystals were collected by filtration
  4. customrecrystallized from a mixed solvent of ethanol
  5. additionaqueous sodium hydroxide solution was added
  6. extractionwas followed by extraction with chloroform
  7. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-0e20dc9cdaf94006819cf687afc16f90
Source dataset
uspto-grants-2001_04
Patent number
US06221864B1

Reaction notes

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