Chloromethyl chloroformate → 2-Benzoylmorpholine hydrochloride

HRID 32310

Reaction equation

HRID 32310 reaction equation
[C:1]([CH:9]1[O:14][CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22]COC(Cl)=O>ClCCCl>[ClH:22].[C:1]([CH:9]1[O:14][CH2:13][CH2:12][NH:11][CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 62754Chloromethyl chloroformateHCID 179717622-Benzoyl-4-benzylmorpholine

Product 1

HCID 688845172-Benzoylmorpholine hydrochlorideYield 67%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-benzoyl-4-benzylmorpholine (600 mg, 2.13 mmol) and chloroformic acid 1-chloromethyl ester (457 mg, 3.20 mmol) in 1,2-dichloroethane (8.0 ml) was refluxed for 1 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (10 ml). The solution was refluxed for 1 h and concentrated under reduced pressure. The crude product was crystallized from ethyl acetate and filtrated to give 2-benzoylmorpholine hydrochloride (323 mg, 67%) as a colorless crystal.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (10 ml)
  3. temperatureThe solution was refluxed for 1 h
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was crystallized from ethyl acetate
  6. filtrationfiltrated

Sources & evidence

ORD record
ord-9f3bad2d120440b88a6b4d3df793da91
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Linked notes

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