Water → HCID 19777235, compound

HRID 1612960Notes

Reaction equation

HRID 1612960 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)C1C=CC=CC=1.C(N(CC)CC)C.[C:23]([Cl:31])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C(Cl)(Cl)Cl>[ClH:31].[C:23]([O:15][CH2:14][CH:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2776358(4-Benzylmorpholin-2-yl)methanol

Product 1

HCID 19777235HCID 19777235, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Benzyl-2-hydroxymethylmorpholine (prepared by the method disclosed in Synthetic Communication, Vol. 10, pages 59-73, 1980) (200 g) and triethylamine (122 g) are dissolved in chloroform (1.5 liter), and thereto is added dropwise benzoyl chloride (135 g) with stirring under ice cooling. The mixture is stirred at room temperature for 16 hours and thereafter to the mixture is added water. The chloroform layer is separated, washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous saline solution in this order, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue is dissolved in ethyl acetate (150 ml) and thereto is added 4N hydrogen chloride/ethyl acetate (250 ml) with stirring under ice cooling, and the precipitated crystals are separated by filtration, washed with ethyl acetate and acetone in this order to give the title compound (240 g) as colorless crystals.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hours
  2. customThe chloroform layer is separated
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous saline solution in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. dissolutionThe residue is dissolved in ethyl acetate (150 ml)
  8. additionis added 4N hydrogen chloride/ethyl acetate (250 ml)
  9. stirringwith stirring under ice cooling
  10. customthe precipitated crystals are separated by filtration
  11. washwashed with ethyl acetate and acetone in this order

Sources & evidence

ORD record
ord-83836314593241a28218164ef6b49fa2
Source dataset
uspto-grants-1993_03
Patent number
US05191079

Reaction notes

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