4-Benzylmorpholine-2-carboxylic acid hydrochloride → Methyl 4-benzylmorpholine-2-carboxylate

HRID 602131

Reaction equation

HRID 602131 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([OH:17])=[O:16])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH3:19]O>>[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([O:17][CH3:19])=[O:16])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochlorideHCID 21893726Hydrochloride methanol

Product 1

HCID 50989152Methyl 4-benzylmorpholine-2-carboxylateYield 80%

Procedure

4-Benzylmorpholine-2-carboxylic acid hydrochloride (1.00 g, 3.88 mmol) in a 10 (w/w) % hydrochloric acid/methanol solution (20 mL) was stirred at room temperature for 2 hours. The solvent was evaporated and a saturated aqueous sodium bicarbonate solution was added to the residue to make the mixture basic. The mixture was then extracted with ethyl acetate and the extract washed with brine and was dried over magnesium sulfate. Evaporation of the solvent gave 730 mg (80%) of the desired compound as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. additiona saturated aqueous sodium bicarbonate solution was added to the residue
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialwas dried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-71ee93e16bae4d76a593d200f4928bb8
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Linked notes

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